Literature DB >> 29215288

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

Naoko Ichiishi1, Christian A Malapit1, Łukasz Woźniak1, Melanie S Sanford1.   

Abstract

This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.

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Year:  2017        PMID： 29215288      PMCID： PMC5772705          DOI： 10.1021/acs.orglett.7b03305

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  41 in total

1.  A prototype of transition-metal-catalyzed carbothiolation of alkynes.

Authors:  K Sugoh; H Kuniyasu; T Sugae; A Ohtaka; Y Takai; A Tanaka; C Machino; N Kambe; H Kurosawa
Journal:  J Am Chem Soc       Date:  2001-05-30       Impact factor: 15.419

2.  Visible-Light-Promoted C-S Cross-Coupling via Intermolecular Charge Transfer.

Authors:  Bin Liu; Chern-Hooi Lim; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2017-09-19       Impact factor: 15.419

3.  Decarbonylative Diaryl Ether Synthesis by Pd and Ni Catalysis.

Authors:  Ryosuke Takise; Ryota Isshiki; Kei Muto; Kenichiro Itami; Junichiro Yamaguchi
Journal:  J Am Chem Soc       Date:  2017-02-22       Impact factor: 15.419

4.  Metallaphotoredox-catalysed sp(3)-sp(3) cross-coupling of carboxylic acids with alkyl halides.

Authors:  Craig P Johnston; Russell T Smith; Simon Allmendinger; David W C MacMillan
Journal:  Nature       Date:  2016-08-17       Impact factor: 49.962

5.  Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Authors:  Christian A Malapit; Naoko Ichiishi; Melanie S Sanford
Journal:  Org Lett       Date:  2017-07-19       Impact factor: 6.005

6.  Transition-metal-free acid-mediated synthesis of aryl sulfides from thiols and thioethers.

Authors:  Anna M Wagner; Melanie S Sanford
Journal:  J Org Chem       Date:  2014-02-19       Impact factor: 4.354

7.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C-N Bond Activation.

Authors:  Jiefeng Hu; Yue Zhao; Jingjing Liu; Yemin Zhang; Zhuangzhi Shi
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-03       Impact factor: 15.336

9.  A general, efficient, and functional-group-tolerant catalyst system for the palladium-catalyzed thioetherification of aryl bromides and iodides.

Authors:  Manuel A Fernández-Rodríguez; John F Hartwig
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

10.  Rhodium-Catalyzed Decarbonylative Borylation of Aromatic Thioesters for Facile Diversification of Aromatic Carboxylic Acids.

Authors:  Hidenori Ochiai; Yuta Uetake; Takashi Niwa; Takamitsu Hosoya
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-26       Impact factor: 15.336
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  10 in total

1.  Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers.

Authors:  Conor E Brigham; Christian A Malapit; Naish Lalloo; Melanie S Sanford
Journal:  ACS Catal       Date:  2020-07-17       Impact factor: 13.084

2.  Metal-catalyzed cross-coupling chemistry with polyhedral boranes.

Authors:  Rafal M Dziedzic; Alexander M Spokoyny
Journal:  Chem Commun (Camb)       Date:  2019-01-03       Impact factor: 6.222

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

Authors:  Chengwei Liu; Michal Szostak
Journal:  ChemCatChem       Date:  2021-09-25       Impact factor: 5.497

4.  Decarbonylative Sulfide Synthesis from Carboxylic Acids and Thioesters via Cross-Over C-S Activation and Acyl Capture.

Authors:  Chengwei Liu; Michal Szostak
Journal:  Org Chem Front       Date:  2021-06-22       Impact factor: 5.456

5.  Nickel-catalyzed reductive thiolation and selenylation of unactivated alkyl bromides.

Authors:  Yi Fang; Torben Rogge; Lutz Ackermann; Shun-Yi Wang; Shun-Jun Ji
Journal:  Nat Commun       Date:  2018-06-08       Impact factor: 14.919

6.  Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide.

Authors:  Ren-Hua Zheng; Hai-Chang Guo; Ting-Ting Chen; Qing Huang; Guo-Bo Huang; Hua-Jiang Jiang
Journal:  RSC Adv       Date:  2018-07-12       Impact factor: 3.361

7.  Metal-free photo-induced sulfidation of aryl iodide and other chalcogenation.

Authors:  Shuai Mao; Yahao Zhao; Zixuan Luo; Ruizhe Wang; Bo Yuan; Jianping Hu; Linghao Hu; San-Qi Zhang; Xiaoxing Ye; Mingliang Wang; Zhengkai Chen
Journal:  Front Chem       Date:  2022-07-26       Impact factor: 5.545

8.  Highly active reduced graphene oxide supported Ni nanoparticles for C-S coupling reactions.

Authors:  Surjyakanta Rana; Jose J Velázquez; S B Jonnalagadda
Journal:  Nanoscale Adv       Date:  2022-07-04

9.  Cobalt-catalyzed intramolecular decarbonylative coupling of acylindoles and diarylketones through the cleavage of C-C bonds.

Authors:  Tian-Yang Yu; Wen-Hua Xu; Hong Lu; Hao Wei
Journal:  Chem Sci       Date:  2020-10-16       Impact factor: 9.825

10.  Deoxygenative trifluoromethylthiolation of carboxylic acids.

Authors:  Runze Mao; Srikrishna Bera; Alexis Cheseaux; Xile Hu
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825
  10 in total

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