Literature DB >> 36213423

Forging C-S Bonds Through Decarbonylation: New Perspectives for the Synthesis of Privileged Aryl Sulfides.

Chengwei Liu1, Michal Szostak2.   

Abstract

Aryl thioethers are tremendously important motifs in various facets of chemical science. Traditional technologies for the precise assembly of aryl thioethers rely on transition-metal-catalyzed cross-coupling of aryl halides; however, despite the continuous advances, the scope of these methods remains limited. Recently a series of reports has advanced an alternative manifold in which thio(esters) are subject to transition-metal-catalyzed decarbonylation, which (1) permits to exploit ubiquitous carboxylic acids as highly desirable and orthogonal precursors to aryl halides; (2) overcomes the issues of high concentration of thiolate anion leading to catalyst poisoning; (3) enables for novel disconnections not easily available from aryl halides; and (4) introduces new concepts in catalysis.

Entities:  

Keywords:  aryl exchange; cross-coupling; decarbonylation; sulfur; thioethers

Year:  2021        PMID: 36213423      PMCID: PMC9534384          DOI: 10.1002/cctc.202101206

Source DB:  PubMed          Journal:  ChemCatChem        ISSN: 1867-3880            Impact factor:   5.497


  33 in total

1.  Electron tomography shows molecular anchoring within a layer-by-layer film.

Authors:  Matthijn R J Vos; Monica Breurken; Philippe E L G Leclère; Paul H H Bomans; Felix de Haas; Peter M Frederik; John A Jansen; Roeland J M Nolte; Nico A J M Sommerdijk
Journal:  J Am Chem Soc       Date:  2008-08-26       Impact factor: 15.419

Review 2.  Carbon-heteroatom bond formation catalysed by organometallic complexes.

Authors:  John F Hartwig
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

3.  Transition-metal-catalyzed C-S, C-Se, and C-Te bond formation via cross-coupling and atom-economic addition reactions.

Authors:  Irina P Beletskaya; Valentine P Ananikov
Journal:  Chem Rev       Date:  2011-03-09       Impact factor: 60.622

4.  Controlled Ni-catalyzed mono- and double-decarbonylations of α-ketothioesters.

Authors:  Zhao-Jing Zheng; Cheng Jiang; Peng-Cheng Shao; Wen-Fei Liu; Tian-Tian Zhao; Peng-Fei Xu; Hao Wei
Journal:  Chem Commun (Camb)       Date:  2019-02-07       Impact factor: 6.222

5.  Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers.

Authors:  Tristan Delcaillau; Philip Boehm; Bill Morandi
Journal:  J Am Chem Soc       Date:  2021-03-03       Impact factor: 15.419

6.  Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers.

Authors:  Naoko Ichiishi; Christian A Malapit; Łukasz Woźniak; Melanie S Sanford
Journal:  Org Lett       Date:  2017-12-07       Impact factor: 6.005

7.  Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation.

Authors:  Chengwei Liu; Chong-Lei Ji; Xin Hong; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-21       Impact factor: 15.336

Review 8.  Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry.

Authors:  Minghao Feng; Bingqing Tang; Steven H Liang; Xuefeng Jiang
Journal:  Curr Top Med Chem       Date:  2016       Impact factor: 3.295

9.  A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols.

Authors:  Manuel A Fernández-Rodríguez; Qilong Shen; John F Hartwig
Journal:  J Am Chem Soc       Date:  2006-02-22       Impact factor: 15.419

10.  Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts.

Authors:  Chengwei Liu; Michal Szostak
Journal:  Chem Commun (Camb)       Date:  2018-02-22       Impact factor: 6.222

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