Showing papers in "Journal of Organic Chemistry in 2015"
TL;DR: A modified probability (DP4+) is developed, whose main differences from the original DP4 are the inclusion of unscaled data and the use of higher levels of theory for the NMR calculation procedure.
Abstract: The DP4 probability is one of the most sophisticated and popular approaches for the stereochemical assignment of organic molecules using GIAO NMR chemical shift calculations when only one set of experimental data is available. In order to improve the performance of the method, we have developed a modified probability (DP4+), whose main differences from the original DP4 are the inclusion of unscaled data and the use of higher levels of theory for the NMR calculation procedure. With these modifications, a significant improvement in the overall performance was achieved, providing accurate and confident results in establishing the stereochemistry of 48 challenging isomeric compounds.
719 citations
TL;DR: A straightforward methodology is adopted to construct a large BN-embedded π-system based on perylene diimide (PDI), which is the first Bn-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons.
Abstract: It is very challenging to introduce azaborine into an electron-deficient arene system because of unfavorable intramolecular electrophilic borylation reaction. In this report, we adopted a straightforward methodology to construct a large BN-embedded π-system based on perylene diimide (PDI), which is the first BN-annulation example with highly electron-withdrawing polycyclic aromatic hydrocarbons. The physical properties of the as-prepared N,N-dicyclohexyl-1-aza-12-bora-benzoperylene diimide (PDI-1BN) have been fully studied, and its sensing behavior to fluoride ion as well as its OLED performance was also investigated.
213 citations
TL;DR: Deuterium labeling and competition experiments reveal that the reductive radical coupling of tertiary N-(acyloxy)phthalimides with electron-deficient alkenes can be terminated by both hydrogen-atom transfer and single-electron reduction followed by protonation, and that this mechanistic duality is controlled by the presence or absence of i-Pr2NEt.
Abstract: Tertiary carbon radicals have notable utility for uniting complex carbon fragments with concomitant formation of new quaternary carbons. This article explores the scope, limitations, and certain mechanistic aspects of Okada’s method for forming tertiary carbon radicals from N-(acyloxy)phthalimides by visible-light photocatalysis. Optimized conditions for generating tertiary radicals from N-(acyloxy)phthalimide derivatives of tertiary carboxylic acids by visible-light irradiation in the presence of 1 mol % of commercially available Ru(bpy)3(PF6)2, diethyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylate (8), and i-Pr2NEt and their coupling in dichloromethane at room temperature with alkene acceptors were developed. Four representative tertiary N-(acyloxy)phthalimides and 15 alkene radical acceptors were examined. Both reductive couplings with electron-deficient alkenes and radical substitution reactions with allylic and vinylic bromides and chlorides were examined with many such reactions occurring in go...
178 citations
TL;DR: A visible light mediated, metal-free process for the thiocyanation of imidazoheterocycles has been developed using eosin Y as a photoredox catalyst under ambient air at room temperature.
Abstract: A visible light mediated, metal-free process for the thiocyanation of imidazoheterocycles has been developed using eosin Y as a photoredox catalyst under ambient air at room temperature. A library of 3-(thiocyanato)imidazo[1,2-a]pyridines with broad functionalities have been synthesized in high yields. This methodology is also applicable for the selenocyanation of imidazo[1,2-a]pyridine.
176 citations
TL;DR: Over the past two decades, organotrifluoroborates have evolved from being chemical curiosities to important reagents for the elaboration of organic molecules, Aside from their often-unique reactivity patterns, favorable features of these reagents include their ease of preparation/isolation, reliable crystallinity, enhanced stability, and monomeric structure.
Abstract: Over the past two decades, organotrifluoroborates have evolved from being chemical curiosities to important reagents for the elaboration of organic molecules. Aside from their often-unique reactivity patterns, favorable features of these reagents include their ease of preparation/isolation, reliable crystallinity, enhanced stability, and monomeric structure. Currently >600 structurally diverse reagents of this class are commercially available, and >850 such compounds have been reported from the author’s laboratory. The organotrifluoroborates can be utilized as shelf-stable precursors to a variety of end products through simple functional group transformations and have also been employed as partners in cross-coupling reactions between aromatic, alkenyl, alkynyl, and alkyl substrates in library or individual formats. Within the realm of cross-coupling reactions, organotrifluoroborates provide a practical entry to substructural entities not readily accessed using other organometallic reagents, and most recen...
163 citations
TL;DR: The first catalytic enantioselective construction of a 3,3'-pyrrolidinyldispirooxindole scaffold has been established via organocatalytic asymmetric 1,3-dipolar cycloadditions of isatin-derived azomethine ylides with methyleneindolinones.
Abstract: The first catalytic enantioselective construction of a 3,3′-pyrrolidinyldispirooxindole scaffold has been established via organocatalytic asymmetric 1,3-dipolar cycloadditions of isatin-derived azomethine ylides with methyleneindolinones, which afforded structurally complex bis-spirooxindoles containing three contiguous and two quaternary stereogenic centers in generally high yields (up to 99%) and excellent diastereo- and enantioselectivities (up to >95:5 dr, 98% ee). This reaction also provides a good example for the application of catalytic asymmetric 1,3-dipolar cycloadditions in constructing enantioenriched bis-spirooxindole frameworks with structural complexity and rigidity.
158 citations
TL;DR: A mild and efficient method for the synthesis of 3-difluoroacetylated coumarins through visible-light-promoted aryldifluoacetylation of alkynes with ethyl bromodifluorosoroacetate has been developed.
Abstract: A mild and efficient method for the synthesis of 3-difluoroacetylated coumarins through visible-light-promoted aryldifluoroacetylation of alkynes with ethyl bromodifluoroacetate has been developed. The reaction allows the direct formation of Csp2–CF2COOEt and C–C bonds via a proposed tandem radical cyclization process.
140 citations
TL;DR: Two new electron-rich fluorescent esters containing a triphenylamine backbone as well as their analogous carboxylic acids have been synthesized and characterized and were found to be quite sensitive for the detection of trace amount of nitroaromatics in solution, solid, and contact mode.
Abstract: This paper demonstrates the role of solvent in selectivity and sensitivity of a series of electron-rich compounds for the detection of trace amounts of picric acid. Two new electron-rich fluorescent esters (6, 7) containing a triphenylamine backbone as well as their analogous carboxylic acids (8, 9) have been synthesized and characterized. Fluorescent triphenylamine coupled with an ethynyl moiety constitutes π-electron-rich selective and sensitive probes for electron-deficient picric acid (PA). In solution, the high sensitivity of all the sensors toward PA can be attributed to a combined effect of the ground-state charge-transfer complex formation and resonance energy transfer between the sensor and analyte. The acids 8 and 9 also showed enhanced sensitivity for nitroaromatics in the solid state, and their enhanced sensitivity could be attributed to exciton migration due to close proximity of the neighboring acid molecules, as evident from the X-ray diffraction study. The compounds were found to be quite sensitive for the detection of trace amount of nitroaromatics in solution, solid, and contact mode.
136 citations
TL;DR: The present method exhibits a mild and selective access to a variety of imidazopyridine derivatives of pharmacological interest.
Abstract: A direct and straightforward approach for highly regioselective thiocyanation of imidazoheterocycles through sp2 C–H functionalization has been realized at room temperature. Various C-3 thiocyanated imidazopyridines are formed in moderate to good yield. The present method exhibits a mild and selective access to a variety of imidazopyridine derivatives of pharmacological interest.
136 citations
TL;DR: This synopsis surveys the various catalytic methods used to access enantioenriched, acyclic α,α-disubstituted α-amino acids with a focus on the processes developed since 2007, when the last major reviews in this area were published.
Abstract: Because of their greater stability and unique conformational properties, unnatural amino acids are highly valued by pharmaceutical, biological, and organic chemists. This synopsis surveys the various catalytic methods used to access enantioenriched, acyclic α,α-disubstituted α-amino acids with a focus on the processes developed since 2007, when the last major reviews in this area were published.
133 citations
TL;DR: This reaction demonstrates that direct C-H activation and the metal carbene migratory insertion can be merged into one catalytic cycle with an Ir(III) complex as the catalyst.
Abstract: Ir(III)-catalyzed coupling of aromatic C–H bonds with diazomalonates has been achieved successfully via a metal carbene migratory insertion process. With different types of carbamoyl directing groups, a wide range of arenes, including heteroarenes, can be used as substrates in this Ir(III)-catalyzed C–H functionalization reaction. Mono- and bisfunctionalized products can be obtained selectively simply by changing the number of equivalents of the diazo substrate. Moreover, when diazomalonates bearing one or two tert-butyl groups are used as the substrates, the C–H bond functionalization is followed by decarboxyation, leading to products with a −CH2CO2Me or −CH2CO2H moiety at the position ortho to the directing group. This reaction demonstrates that direct C–H activation and the metal carbene migratory insertion can be merged into one catalytic cycle with an Ir(III) complex as the catalyst.
TL;DR: An overview of the factors that lead to high-spin ground states as well as recent progress in the design and synthesis of high- spin organic molecules is provided.
Abstract: Organic molecules with high-spin ground states, besides being fundamentally interesting, possess numerous potential applications in diverse fields such organic magnetism, MRI contrast agents, and spintronics. Such molecules, once thought to exist only as highly reactive intermediates, can be rationally designed to have adequate stability for organic synthesis and characterization. This Synopsis provides an overview of the factors that lead to high-spin ground states as well as recent progress in the design and synthesis of high-spin organic molecules.
TL;DR: A novel and convenient silver-mediated radical cyclization method for the synthesis of coumarin derivatives via the direct difunctionalization of alkynoates with α-keto acids through double C-C bond formation under mild conditions has been developed.
Abstract: A novel and convenient silver-mediated radical cyclization method for the synthesis of coumarin derivatives via the direct difunctionalization of alkynoates with α-keto acids through double C–C bond formation under mild conditions has been developed. This new method is highly efficient and practical, and the starting materials are readily prepared. The present method should provide a useful strategy for the construction of coumarin motifs.
TL;DR: Two new classes of highly active yet air- and moisture-stable π-R-allylpalladium complexes containing bulky biaryl- and bipyrazolylphosphines with extremely broad ligand scope have been developed, highlighting the versatility and practicality of these catalysts in organic synthesis.
Abstract: Two new classes of highly active yet air- and moisture-stable π-R-allylpalladium complexes containing bulky biaryl- and bipyrazolylphosphines with extremely broad ligand scope have been developed. Neutral π-allylpalladium complexes incorporated a range of biaryl/bipyrazolylphosphine ligands, while extremely bulky ligands were accommodated by a cationic scaffold. These complexes are easily activated under mild conditions and are efficient for a wide array of challenging C-C and C-X (X = heteroatom) cross-coupling reactions. Their high activity is correlated to their facile activation to a 12-electron-based "L-Pd(0)" catalyst under commonly employed conditions for cross-coupling reactions, noninhibitory byproduct release upon activation, and suppression of the off-cycle pathway to form dinuclear (μ-allyl)(μ-Cl)Pd2(L)2 species, supported by structural (single crystal X-ray) and kinetic studies. A broad scope of C-C and C-X coupling reactions with low catalyst loadings and short reaction times highlight the versatility and practicality of these catalysts in organic synthesis.
TL;DR: A simplified electrophilic trifluoromethylthiolating reagent 1c was identified that can react with a wide range of nucleophiles such as Grignard reagents, arylboronic acids, alkynes, indoles, β-ketoesters, oxindoles, and sodium sulfinates under mild reaction conditions.
Abstract: A family of electrophilic trifluoromethanesulfenates was prepared Structure–reactivity relationship studies showed that the substituted groups on the aryl ring of the trifluoromethylthiolating reagent did not have an obvious influence on their reactivities A simplified electrophilic trifluoromethylthiolating reagent 1c was then identified that can react with a wide range of nucleophiles such as Grignard reagents, arylboronic acids, alkynes, indoles, β-ketoesters, oxindoles, and sodium sulfinates under mild reaction conditions A variety of functional groups were tolerated under these conditions
TL;DR: The first catalytic asymmetric 1,3-dipolar cycloadditions of isatin-derived azomethine ylide with allenes have been established, which efficiently assembly isatins, amino-esters and 2, 3-allenoate into enantioenriched spiro[indoline-3,2'-pyrrole] derivatives with a quaternary stereogenic center in generally high enantioselectivities.
Abstract: The first catalytic asymmetric 1,3-dipolar cycloadditions (1,3-DCs) of isatin-derived azomethine ylide with allenes have been established, which efficiently assembly isatins, amino-esters and 2,3-allenoate into enantioenriched spiro[indoline-3,2′-pyrrole] derivatives with a quaternary stereogenic center in generally high enantioselectivities (80–98% ee). In this allene-involved 1,3-DC, an unexpected spirooxindole framework bearing an intra-annular C═C double bond was generated, which is quite different from previously reported 1,3-DCs of allenes. This approach not only confronted the great challenge in using allenes as dipolarophiles of 1,3-DCs, but also provided a unique strategy of using allenes as equivalents of alkynes to construct spiro[indoline-3,2′-pyrrole] structure. Besides, this reaction also represents the first catalytic asymmetric ketone-involved 1,3-DCs of allenes, which will also greatly enrich the research contents of 1,3-DCs, the chemistry of allenes as well as the synthetic methods of sp...
TL;DR: A new approach to the selective synthesis of (E)-vinyl sulfones has been developed via a Fe/Cu co-catalyzed sulfonylation of arylpropiolic acid or phenylacetylene with sulfonyl hydrazides, comparable to the best results reported so far.
Abstract: A new approach to the selective synthesis of (E)-vinyl sulfones has been developed via a Fe/Cu co-catalyzed sulfonylation of arylpropiolic acid or phenylacetylene with sulfonyl hydrazides. A variety of vinyl sulfones have been obtained in moderate to good yields, comparable to the best results reported so far. The inexpensive Fe/Cu co-catalyzed method features a simple experimental procedure and good tolerance of substrate.
TL;DR: A formal 1,6-conjugated addition-mediated [2+1] annulation to synthesize spiro[2.5]octa-4,7-dien-6-one with p-quinone methides and sulfur ylides has been described and exhibited good functional group tolerance and scalability without the use of metals and bases.
Abstract: A formal 1,6-conjugated addition-mediated [2+1] annulation to synthesize spiro[2.5]octa-4,7-dien-6-one with p-quinone methides and sulfur ylides has been described. This domino-type process was highly diastereoselective and exhibited good functional group tolerance and scalability without the use of metals and bases.
TL;DR: The reaction is performed in a tandem manner constituted by the sequential sulfonylation of alkynes, ipso-carbocyclization, dearomatization, hydration, and oxidation processes, providing a convenient and efficient approach to various sulfonated azaspiro[4,5] trienones of biological importance.
Abstract: A novel and direct oxidative spirocyclization of arylpropiolamides with sulfonylhydrazides leading to 3-sulfonated azaspiro[4,5]trienones has been developed under metal-free conditions. The reaction is performed in a tandem manner constituted by the sequential sulfonylation of alkynes, ipso-carbocyclization, dearomatization, hydration, and oxidation processes, providing a convenient and efficient approach to various sulfonated azaspiro[4,5] trienones of biological importance.
TL;DR: The OLED with 2c emits a strong green light at a peak of 536 nm with a maximum luminance of the OLED of about 8600 cd m(-2), which indicates that 2c could be a promising fluorescent dye for OLED applications.
Abstract: Realizing the control of emission colors of single molecules is very important in the development of full-color emitting materials. Herein, three novel phenazine derivatives (2,3,7,8-tetrakis(decyloxy)phenazine (2a), 2,3-didecyloxy-5,14-diaza-7,12-dioxo-9,10- dicyanopentacene (2b), and 2,3,13,14-tetradecyloxy-5,11,16,22-tetraaza-7,9,18,20-tetraoxo-8,19-dicyanoenneacene (2c)) have been successfully synthesized and fully characterized. Compound 2c can emit blue light in toluene solution (450 nm), green light in the powder/film state (502/562 nm), and red light in the 2c/TFA state (610 nm). The OLED with 2c emits a strong green light at a peak of 536 nm with a maximum luminance of the OLED of about 8600 cd m(-2), which indicates that 2c could be a promising fluorescent dye for OLED applications.
TL;DR: A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described, providing an efficient approach for the synthesis of α-aryl-β-trifluors amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.
Abstract: A novel visible-light-induced trifluoromethylarylation/1,4-aryl shift/desulfonylation cascade reaction using CF3SO2Cl as CF3 source was described. The protocol provides an efficient approach for the synthesis of α-aryl-β-trifluoromethyl amides and/or CF3-containing oxindoles as well as the isoquinolinediones under benign conditions.
TL;DR: A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have been synthesized regioselectively and carried out at room temperature through the functionalization of the sp(2) C-H bond employing Langlois reagent under ambient air.
Abstract: Catalytic oxidative trifluoromethylation of imidazopyridines has been carried out at room temperature through the functionalization of the sp2 C–H bond employing Langlois reagent under ambient air. A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have been synthesized regioselectively. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.
TL;DR: An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst, found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones.
Abstract: An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.
TL;DR: A solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation is reported.
Abstract: Herein, we report a solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation. This eco-friendly approach afforded the desired products in good to excellent yields in only 10 min. In addition, using the same protocol, we carried out the cyclization reaction of relevant molecules, such as lapachol derivatives.
TL;DR: This work reports the Pd@PANI-catalyzed Heck reactions with very wide substrate scopes, and discloses the catalytic mechanisms based on experimental findings and results of catalyst analysis and characterization.
Abstract: Using air as the oxidant instead of the traditionally employed persulfates, the smaller and more uniform Pd nanoparticles (around 2 nm) supported on polyaniline (Pd@PANI) can be easily fabricated by the oxidation-polymerization of aniline with PdCl2. This material is an efficient and environmentally friendly catalyst for Heck reactions due to its recyclability, low loading, and ligand-free and mild reaction conditions. It was even tolerant to sulfur-containing substrates. This work reports the Pd@PANI-catalyzed Heck reactions with very wide substrate scopes, and discloses the catalytic mechanisms based on experimental findings and results of catalyst analysis and characterization.
TL;DR: This work found larger SOC and smaller singlet-triplet energy gaps for the thiophene-fused BODIPY derivative and their results are useful for studies of the photochemistry of organic chromophores.
Abstract: A thiophene-fused BODIPY chromophore displays a large triplet-state quantum yield (ΦT = 63.7%). In contrast, when the two thienyl moieties are not fused into the BODIPY core, intersystem crossing (ISC) becomes inefficient and ΦT remains low (ΦT = 6.1%). First-principles calculations including spin-orbit coupling (SOC) were performed to quantify the ISC. We found larger SOC and smaller singlet-triplet energy gaps for the thiophene-fused BODIPY derivative. Our results are useful for studies of the photochemistry of organic chromophores.
TL;DR: Rh(III)-catalyzed C-H activation of 2-phenylimidazo[1,2-a]pyridines in divergent oxidative coupling with alkynes has been achieved and a rhodacyclic intermediate has been isolated.
Abstract: Rh(III)-catalyzed C–H activation of 2-phenylimidazo[1,2-a]pyridines in divergent oxidative coupling with alkynes has been achieved. Selective mono versus 2-fold C–H activation has been attained under condition control. When AgOAc was used as an oxidant, the coupling afforded 5,6-disubstituted naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines as a result of initial nitrogen chelation-assisted C–H activation at the benzene ring followed by rollover C–H activation. In contrast, the reaction afforded a fused isoquinolinium salt as a result of C–C and C–N coupling when AgBF4 was employed as a co-oxidant. A rhodacyclic intermediate has been isolated.
TL;DR: A combined theoretical and experimental study of the initial tautomerization rate of a range of phosphinylidene compounds establishes a quantitative measure for the reactivity of various phosphorus compounds, as well as an accurate predictive tool.
Abstract: Phosphinylidene compounds R1R2P(O)H are important functionalities in organophosphorus chemistry and display prototropic tautomerism. Quantifying the tautomerization rate is paramount to understanding these compounds’ tautomerization behavior, which may impact their reactivities in various reactions. We report a combined theoretical and experimental study of the initial tautomerization rate of a range of phosphinylidene compounds. Initial tautomerization rates are found to decrease in the order H3PO2 > Ph2P(O)H > (PhO)2P(O)H > PhP(O) (OAlk)H > AlkP(O)(OAlk)H ≈ (AlkO)2P(O)H, where “Alk” denotes an alkyl substituent. The combination of computational investigations with experimental validation establishes a quantitative measure for the reactivity of various phosphorus compounds, as well as an accurate predictive tool.
TL;DR: These studies demonstrated a framework for characterization of five-coordinate trigonal bipyramidal vanadium inhibitors by comparison with the reported vanadium-protein phosphatase complexes, and suggest that if effective delivery of potentially active antidiabetic compound such a the organic vanadate peptidic substrate was possible the toxicity problems currently reported for the salts and some of the complexes may be alleviated and dramatic enhancement of antidi diabetic vanadium compounds may result.
Abstract: Studies of antidiabetic vanadium compounds, specifically the organic vanadate esters, are reviewed with regard to their chemistry and biological properties. The compounds are described from the perspective of how the fundamental chemistry and properties of organic vanadate esters impact their effects as inhibitors for phosphatases based on the structural information obtained from vanadium-phosphatase complexes. Vanadium compounds have been reported to have antidiabetic properties for more than a century. The structures and properties of organic vanadate complexes are reviewed, and the potency of such vanadium coordination complexes as antidiabetic agents is described. Because such compounds form spontaneously in aqueous environments, the reactions with most components in any assay or cellular environment has potential to be important and should be considered. Generally, the active form of vanadium remains elusive, although studies have been reported of a number of promising vanadium compounds. The description of the antidiabetic properties of vanadium compounds is described here in the context of recent characterization of vanadate-phosphatase protein structures by data mining. Organic vanadate ester compounds are generally four coordinate or five coordinate with the former being substrate analogues and the latter being transition-state analogue inhibitors. These studies demonstrated a framework for characterization of five-coordinate trigonal bipyramidal vanadium inhibitors by comparison with the reported vanadium-protein phosphatase complexes. The binding of the vanadium to the phosphatases is either as a five-coordinate exploded transition-state analogue or as a high energy intermediate, respectively. Even if potency as an inhibitor requires trigonal bipyramidal geometry of the vanadium when bound to the protein, such geometry can be achieved upon binding from compounds with other geometries. Desirable properties of ligands are identified and analyzed. Ligand interactions, as reported in one peptidic substrate, are favorable so that complementarity between phosphatase and coordinating ligand to the vanadium can be established resulting in a dramatic enhancement of the inhibitory potency. These considerations point to a frameshift in ligand design for vanadium complexes as phosphatase inhibitors and are consistent with other small molecule having much lower affinities. Combined, these studies do suggest that if effective delivery of potentially active antidiabetic compound such a the organic vanadate peptidic substrate was possible the toxicity problems currently reported for the salts and some of the complexes may be alleviated and dramatic enhancement of antidiabetic vanadium compounds may result.
TL;DR: A novel and highly regioselective ammonium iodide-induced nonradical sulfenylation method for the construction of a C-S bond was developed via C-H functionalization, making it a highly valuable and practical method in pharmaceutical industry.
Abstract: A novel and highly regioselective ammonium iodide-induced nonradical sulfenylation method for the construction of a C–S bond was developed via C–H functionalization. With DMSO or R1SO2NHNH2 as a sulfenylating agent, MeS- and R1S-substituted flavone derivatives were obtained in good yields. This method enriches current C–S bond formation chemistry, making it a highly valuable and practical method in pharmaceutical industry.