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Showing papers in "Organic Letters in 2014"


Journal ArticleDOI
TL;DR: A C-P bond and a C-C bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors.

223 citations


Journal ArticleDOI
TL;DR: A copper-catalyzed alkylarylation of alkenes with simple alkanes was achieved, which not only provided an efficient method to prepare variousAlkyl-substituted oxindoles, but also represented a novel strategy for selective sp(3) C-H functionalization/C-C bond formation via a free-radical cascade process.

216 citations


Journal ArticleDOI
TL;DR: This method provided a general way to construct fluorinated 2-oxindoles from reaction with N-arylacrylamides via a proposed tandem radical cyclization process.

215 citations


Journal ArticleDOI
TL;DR: A practical and unified strategy has been described for the preparation of mono- and difluoromethylated phenanthridine derivatives using a visible-light-promoted alkylation and decarboxylation sequence from biphenyl isocyanides with ethyl bromofluoroacetate (EBFA) or ethylbromodifluoro acetate (EBDFA).

213 citations


Journal ArticleDOI
TL;DR: Photoredox-catalyzed vicinal chlorotrifluoromethylation of alkene is described, suggesting that the method could be feasible for late-stage modification in drug discovery.

212 citations


Journal ArticleDOI
TL;DR: A method for cobalt-catalyzed, aminoquinoline-directed ortho-functionalization of sp2 C–H bonds with alkenes has been developed and excellent functional group tolerance is observed.

208 citations


Journal ArticleDOI
TL;DR: The Rh(III)-catalyzed C-8 selective direct alkylation and alkynylation of quinoline N-oxides has been developed and demonstrates the synthetic utility of the N-oxide directing group as a stepping stone for remote C-H functionalized quinolines.

198 citations


Journal ArticleDOI
TL;DR: Iodine-catalyzed selective 2-arylsulfonyl indole formation from indoles and sodium sulfinates is disclosed.

177 citations


Journal ArticleDOI
TL;DR: A method for direct carbonylation of aminoquinoline benzamides has been developed andBenzoic and acrylic acid derivatives can be carbonylated by carbon monoxide affording imides in good yields.

176 citations


Journal ArticleDOI
TL;DR: A Cu-catalyzed intramolecular C-H amination for the synthesis of carbazoles has been developed and its mild oxidation aptitude enables the rapid and concise construction of heteroatom-incorporated carbazole core π-systems.

176 citations


Journal ArticleDOI
TL;DR: This protocol utilizes [18F]KF to access 18F-labeled electron-rich, -neutral, and -deficient aryl fluorides under a single set of mild conditions to access protected versions of two important radiotracers.

Journal ArticleDOI
TL;DR: A method for monotrifluoromethylthiolation of arenes via palladium-catalyzed directed C-H bond activation was described, and initial mechanistic studies disclosed that the turnover limiting step of the catalytic cycle did not involve C- H activation.

Journal ArticleDOI
TL;DR: A novel method for visible-light photoredox-catalyzed difluoromethylation of electron-rich N-, O-, and S-containingheteroarenes under mild reaction conditions is developed.

Journal ArticleDOI
TL;DR: The addition of Grignard reagents or organolithium reagents to the SO2-surrogate DABSO generates a diverse set of metal sulfinates, suitable for direct conversion to sulfone products.

Journal ArticleDOI
TL;DR: Under the optimized conditions using [Ru(bpy)3(PF6)2] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nucleophiles.

Journal ArticleDOI
TL;DR: A HKOCl-2 series of new fluorescent probes for hypochlorous acid (HOCl) detection in live cells is reported, which exhibit excellent selectivity, sensitivity, and chemostability toward HOCl.

Journal ArticleDOI
Xia Mi1, Chenyang Wang1, Mengmeng Huang1, Jianye Zhang1, Yusheng Wu1, Yangjie Wu1 
TL;DR: Ag2CO3-catalyzed difunctionalization of alkynes via a radical phosphonation and C-H functionalization tandem process was developed to synthesize various 3-phosphonated coumarins in moderate to high yields with high regioselectivity.

Journal ArticleDOI
TL;DR: The first example of silver-mediated oxidative aryltrifluoromethylthiolation of activated alkenes to produce valuable trifluors containing oxindoles was developed, providing a practical and easy-handling method to generate a F3CS(•) radical in the laboratory.

Journal ArticleDOI
TL;DR: Regioselective sulfenylation of imidazoheterocycles with thiophenols at room temperature is reported and N-chlorosuccinimide is promoted under metal-free conditions with a broad range of substrate scopes.

Journal ArticleDOI
TL;DR: A highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described and a single electron transfer (SET)-mediated mechanism is proposed.

Journal ArticleDOI
TL;DR: In this article, a new air-stable nickel precatalyst for C-N cross-coupling is reported, which is compatible with a weak base, allowing the amination of substrates containing base-sensitive functional groups.

Journal ArticleDOI
TL;DR: A nitrile-based template attached with a phenylacetic acid framework promoted meta-selective C-H bond olefination and the versatility of this operationally simple method has been demonstrated through drug diversification.

Journal ArticleDOI
TL;DR: A copper-catalyzed free-radical cascade cyclization of isocyanides with simple alkanes and alcohols was developed, which allowed convenient access to various alkyl-substituted phenanthridines.

Journal ArticleDOI
TL;DR: Under the optimized conditions using [Ru(bpy)3(PF6)2] as the photocatalyst and Umemoto's reagent as the CF3 source, a wide range of substituted styrenes as well as various activated and nonactivated alkenes can readily be difunctionalized, affording β-trifluoromethylated azides or amines in good yields.

Journal ArticleDOI
TL;DR: A copper-mediated C-S/N-S bond-forming reaction via C-H activation that uses elemental sulfur has been developed, providing efficient and practical access to benzoisothiazolones.

Journal ArticleDOI
TL;DR: The first example of a metal-free direct carbotrifluoromethylation of alkenes using inexpensive TMSCF3 as the CF3 source is described.

Journal ArticleDOI
TL;DR: This novel methodology provides an efficient approach to vicinal amino azides which can easily be transformed into other valuable amine derivatives.

Journal ArticleDOI
TL;DR: Electron spin resonance (ESR) studies indicate that atom-transfer processes are involved in this system and this strategy allows highly selective access to a variety of CF(3)-containing oxindoles and pyrrolidines.

Journal ArticleDOI
TL;DR: The transformation has demonstrated for the first time that Cu(OAc)2 can be renewable after undergoing an oxidative reaction, and offers a highly efficient approach to the 3-methyleneisoindolin-1-one scaffold.

Journal ArticleDOI
TL;DR: The red-shifted telluride version of the annulated BODIPY selenide product was found to be sensitive and selective for hypochlorite detection, reversible upon treatment with biothiols.