Literature DB >> 28723158

Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides.

Christian A Malapit1, Naoko Ichiishi1, Melanie S Sanford1.   

Abstract

This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.

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Year:  2017        PMID: 28723158      PMCID: PMC5565168          DOI: 10.1021/acs.orglett.7b02024

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


  40 in total

1.  Decarboxylative borylation.

Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

2.  Synthesis of Biaryls through Nickel-Catalyzed Suzuki-Miyaura Coupling of Amides by Carbon-Nitrogen Bond Cleavage.

Authors:  Shicheng Shi; Guangrong Meng; Michal Szostak
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-21       Impact factor: 15.336

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.  An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Jun Pan; Xinyan Wang; Yong Zhang; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-08-24       Impact factor: 6.005

5.  Dual catalysis. Merging photoredox with nickel catalysis: coupling of α-carboxyl sp³-carbons with aryl halides.

Authors:  Zhiwei Zuo; Derek T Ahneman; Lingling Chu; Jack A Terrett; Abigail G Doyle; David W C MacMillan
Journal:  Science       Date:  2014-06-05       Impact factor: 47.728

6.  Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

7.  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

8.  A palladium-catalyzed carbonylation approach to acid chloride synthesis.

Authors:  Jeffrey S Quesnel; Bruce A Arndtsen
Journal:  J Am Chem Soc       Date:  2013-10-29       Impact factor: 15.419

9.  An Exclusively trans-Selective Chlorocarbamoylation of Alkynes Enabled by a Palladium/Phosphaadamantane Catalyst.

Authors:  Christine M Le; Xiao Hou; Theresa Sperger; Franziska Schoenebeck; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-20       Impact factor: 15.336

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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  9 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.  Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source.

Authors:  Yong Ho Lee; Elliott H Denton; Bill Morandi
Journal:  Nat Chem       Date:  2021-01-29       Impact factor: 24.427

3.  Decarbonylative Pd-Catalyzed Suzuki Cross-Coupling for the Synthesis of Structurally Diverse Heterobiaryls.

Authors:  Alejandro Cervantes-Reyes; Aaron C Smith; Gary M Chinigo; David C Blakemore; Michal Szostak
Journal:  Org Lett       Date:  2022-02-24       Impact factor: 6.072

4.  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

5.  Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.

Authors:  Tongliang Zhou; Pei-Pei Xie; Chong-Lei Ji; Xin Hong; Michal Szostak
Journal:  Org Lett       Date:  2020-08-10       Impact factor: 6.005

6.  Investigation of the Selectivity of the Palladium-Catalyzed Aroylation and Arylation of Stannyl Glycals with Aroyl Chlorides.

Authors:  Tsuyoshi Shinozuka
Journal:  ACS Omega       Date:  2021-03-19

7.  N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki-Miyaura Cross Coupling.

Authors:  Emily K Reeves; Jenna N Humke; Sharon R Neufeldt
Journal:  J Org Chem       Date:  2019-09-11       Impact factor: 4.198

8.  Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides.

Authors:  Sinead T Keaveney; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-13       Impact factor: 15.336

9.  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

  9 in total

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