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Jin Huang

Bio: Jin Huang is an academic researcher from Sichuan University. The author has contributed to research in topics: Claisen rearrangement & Catalysis. The author has an hindex of 4, co-authored 5 publications receiving 41 citations.

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TL;DR: A simple and recyclable catalytic system for direct arylation of heteroarenes via C–H bond activation was developed with a relatively inexpensive RuCl3·xH2O as a catalyst and PEG-400 as a green medium without any additive or ligand that showed excellent functional group compatibility.
Abstract: A simple and recyclable catalytic system for direct arylation of heteroarenes via C–H bond activation was developed with a relatively inexpensive RuCl3·xH2O as a catalyst and PEG-400 as a green medium without any additive or ligand. This system not only showed excellent functional group compatibility, but also the ratio of mono- to diarylated product was easily regulated by varying the reaction conditions. Moreover, this transformation could proceed under air and be easily scaled up to gram-scale in a low catalyst loading of 0.3 mol%. Particularly, a good yield of 85% was obtained after this catalyst was recycled six times.

16 citations

Journal ArticleDOI
Jin Huang1, Wei Wang1, Hai-Yu He1, Lei Jian1, Haiyan Fu1, Xueli Zheng1, Hua Chen1, Ruixiang Li1 
TL;DR: Mechanistic studies confirm that 1-propenylnaphthols are the key intermediates to form the 3-arylnaphtho[2,1-b]furans and these two operationally simple and practical protocols could be scaled up to a gram level.
Abstract: A simple and efficient strategy for the synthesis of 1-propenylnaphthols from readily accessible 3-arylallylnaphthyl ethers has been developed. By using K2CO3 as base and 2-methoxyethanol as solvent, direct access to a wide range of 1-propenylnaphthols can be achieved in generally good yield (up to 99%) with high stereoselectivity toward the Z isomer. The control experiments indicate that the reaction proceeds through a sequential Claisen rearrangement/isomerization process. Furthermore, starting from the same material, the highly valuable 3-arylnaphtho[2,1-b]furans can be obtained in N,N-dimethylformamide and in the presence of Ag2O as the oxidant via a one-pot sequential Claisen rearrangement/isomerization/cyclization reaction. Mechanistic studies confirm that 1-propenylnaphthols are the key intermediates to form the 3-arylnaphtho[2,1-b]furans. In addition, these two operationally simple and practical protocols could be scaled up to a gram level.

14 citations

Journal ArticleDOI
TL;DR: The palladium-catalyzed domino intermolecular C(sp2)–H activation reaction of two aryl iodides was explored and showed good activity.

8 citations


Cited by
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TL;DR: In this article, a general perspective of biomass-derived solvents for transition metal-catalyzed C-H activation reactions and their unique potential for chemical syntheses up to January 2019 is presented.
Abstract: Transition metal-catalyzed C–H activation has emerged as an increasingly powerful strategy in molecular syntheses and a particularly attractive alternative to classical methods of cross-couplings. During the recent years, significant focus has been dedicated to further improve the sustainable nature of the C–H activation approach. As solvents represent a major portion of organic pollution caused by chemical syntheses, a range of nontoxic, biobased, sustainable solvents have been developed to substitute for common organic reaction media. In this review, we present a general perspective of biomass-derived solvents for transition metal-catalyzed C–H activation reactions and their unique potential for chemical syntheses up to January 2019.

81 citations

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TL;DR: Recent developments which utilize these σ‐alky‐PdII‐species for remote C−H functionalization to reinvigorate new C−C bond formation in cascade fashion via use of catalytic palladium metal are highlighted.
Abstract: The transition-metal-directed C−H activation processes have traditionally required the installation of suitable coordinating groups to place the metal in close proximity to an specific neighboring or remote C(sp2)-H or C(sp3)-H moiety of the molecular structure. Alternatively, substitution of C−H bonds at positions previously thought inaccessible are now performed through domino processes via in situ generated σ-alkyl-PdII species. This Concept article highlights on recent developments which utilize these σ-alky-PdII-species for remote C−H functionalization to reinvigorate new C−C bond formation in cascade fashion via use of catalytic palladium metal.

63 citations

Journal ArticleDOI
TL;DR: A novel palladium-catalyzed [4+1] spiroannulation was developed by using a C(sp3 )-H activation/naphthol dearomatization approach, rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional-group tolerance.
Abstract: A novel palladium-catalyzed [4+1] spiroannulation was developed by using a C(sp3 )-H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation-facilitated C(sp3 )-H activation, biaryl cross-coupling, and naphthol dearomatization, thus rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional-group tolerance. Preliminary mechanistic studies indicate that C-H cleavage is likely involved in the rate-determining step, and a five-membered palladacycle was identified as the key intermediate for the intermolecular coupling.

63 citations

Journal ArticleDOI
TL;DR: In this paper, the first tandem iridium catalysis was reported for axially chiral styrenes enabled by asymmetric Allylic Substitution-Isomerization (AASI) using cinnamyl carbonate analogues as electrophiles and naphthols as nucleophiles.
Abstract: Axially chiral styrenes are of great interest since they may serve as a class of novel chiral ligands in asymmetric synthesis. However, only recently have strategies been developed for their enantioselective preparation. Thus, the development of novel and efficient methodologies is highly desirable. Herein, we reported the first tandem iridium catalysis as a general strategy for the synthesis of axially chiral styrenes enabled by Asymmetric Allylic Substitution-Isomerization (AASI) using cinnamyl carbonate analogues as electrophiles and naphthols as nucleophiles. In this approach, axially chiral styrenes were generated through two independent iridium-catalytic cycles: iridium-catalyzed asymmetric allylic substitution and in situ isomerization via stereospecific 1,3-hydride transfer catalyzed by the same iridium catalyst. Both experimental and computational studies demonstrated that the isomerization proceeded by iridium-catalyzed benzylic C-H bond oxidative addition, followed by terminal C-H reductive elimination. Amid the central-to-axial chirality transfer, the hydroxyl of naphthol plays a crucial role in ensuring the stereospecificity by coordinating with the Ir(I) center. The process accommodated broad functional group compatibility. The products were generated in excellent yields with excellent to high enantioselectivities, which could be transformed to various axially chiral molecules.

50 citations

Journal ArticleDOI
TL;DR: This review will provide an introduction to transition metal-catalyzed C-H activation for the synthesis of polycycles, helping researchers to discover indirect connections and reveal hidden opportunities, and promote the discovery of novel synthetic strategies relying on C- H activation.
Abstract: Polycycles are abundantly present in numerous advanced chemicals, functional materials, bioactive molecules and natural products. However, the strategies for the synthesis of polycycles are limited to classical reactions and transition metal-catalyzed cross-coupling reactions, requiring pre-functionalized starting materials and lengthy synthetic operations. The emergence of novel approaches shows great promise for the fields of organic/medicinal/materials chemistry. Among them, transition metal-catalyzed C-H activation followed by intermolecular annulation reactions prevail, due to their straightforward manner with high atom- and step-economy, providing rapid, concise and efficient methods for the construction of diverse polycycles. Several strategies have been developed for the synthesis of polycycles, relying on sequential multiple C-H activation/annulation, or combination of C-H activation/annulation and further interaction with a proximal group, or merger of C-H activation with a cycloaddition reaction, or in situ formation of the directing group. These are attractive, efficient, step- and atom-economic methods starting from commercially available materials. This Minireview will provide an introduction to transition metal-catalyzed C-H activation for the synthesis of polycycles, helping researchers to discover indirect connections and reveal hidden opportunities. It will also promote the discovery of novel synthetic strategies relying on C-H activation.

46 citations