Journal ArticleDOI
Transition-metal-catalyzed C-S bond coupling reaction.
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TLDR
Recent efforts in metal-catalyzed C-S bond cross-coupling reactions are summarized, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.Abstract:
Sulfur-containing molecules such as thioethers are commonly found in chemical biology, organic synthesis, and materials chemistry. While many reliable methods have been developed for preparing these compounds, harsh reaction conditions are usually required in the traditional methods. The transition metals have been applied in this field, and the palladium-catalyzed coupling of thiols with aryl halides and pseudo halides is one of the most important methods in the synthesis of thioethers. Other metals have also been used for the same purpose. Here, we summarize recent efforts in metal-catalyzed C-S bond cross-coupling reactions, focusing especially on the coupling of thiols with aryl- and vinyl halides based on different metals.read more
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Organometallic palladium reagents for cysteine bioconjugation
Ekaterina V. Vinogradova,Chi Zhang,Alexander M. Spokoyny,Bradley L. Pentelute,Stephen L. Buchwald +4 more
TL;DR: It is reported that palladium(ii) complexes can be used for efficient and highly selective cysteine conjugation (bioconjugation) reactions that are rapid and robust under a range of bio-compatible reaction conditions.
Journal ArticleDOI
External Oxidant-Free Oxidative Cross-Coupling: A Photoredox Cobalt-Catalyzed Aromatic C-H Thiolation for Constructing C-S Bonds.
Guoting Zhang,Chao Liu,Hong Yi,Qing-Yuan Meng,Changliang Bian,Hong Chen,Jing-Xin Jian,Li-Zhu Wu,Aiwen Lei +8 more
TL;DR: The kinetic studies indicate that the interaction between the cobalt catalyst and proton might be involved in the rate-limiting process and the unexpected oxidation byproduct amides, which are often generated in oxidative cyclization of thiobenzanilides, can be completely avoided.
Journal ArticleDOI
Electrocatalytic Oxidant‐Free Dehydrogenative C−H/S−H Cross‐Coupling
TL;DR: An environmentally friendly electrocatalytic protocol has been developed for dehydrogenative C-H/S-H cross-coupling and it is indicated that the generation of aryl radical cation intermediates is key to the success of this transformation.
Organometallic palladium reagents for cysteine bioconjugation
Ekaterina V. Vinogradova,Chi Zhang,Alexander M. Spokoyny,Bradley L. Pentelute,Stephen L. Buchwald +4 more
TL;DR: In this article, the palladium(II) complexes were used for efficient and highly selective cysteine conjugation (bioconjugation) reactions that are rapid and robust under a range of bio-compatible reaction conditions.
Journal ArticleDOI
Fundamental Studies and Development of Nickel-Catalyzed Trifluoromethylthiolation of Aryl Chlorides: Active Catalytic Species and Key Roles of Ligand and Traceless MeCN Additive Revealed
TL;DR: A catalytic protocol to convert aryl and heteroaryl chlorides to the corresponding trifluoromethyl sulfides and its beneficial role lies in decreasing the energetic span, therefore accelerating product formation.
References
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Modern Synthetic Methods for Copper‐Mediated C(aryl) ? O, C(aryl) ? N, and C(aryl) ? S Bond Formation
Steven V. Ley,Andrew Thomas +1 more
TL;DR: In this article, the authors highlight the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids as reaction partners in both O- and N-arylation.
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Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
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Thiol-ene “click” reactions and recent applications in polymer and materials synthesis
TL;DR: In this paper, a review highlights examples of recent applications of both the radical-mediated and base/nucleophile-initiated thiol-ene reactions in polymer and materials synthesis.
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