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 <span class="Chemical">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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