Literature DB >> 32806154

Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.

Tongliang Zhou1, Pei-Pei Xie2, Chong-Lei Ji2, Xin Hong2, Michal Szostak1.   

Abstract

Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.

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Year:  2020        PMID: 32806154      PMCID: PMC7456303          DOI: 10.1021/acs.orglett.0c02250

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


  42 in total

1.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

2.  Directed Decarbonylation of Unstrained Aryl Ketones via Nickel-Catalyzed C-C Bond Cleavage.

Authors:  Tian-Tian Zhao; Wen-Hua Xu; Zhao-Jing Zheng; Peng-Fei Xu; Hao Wei
Journal:  J Am Chem Soc       Date:  2018-01-08       Impact factor: 15.419

3.  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

Review 4.  Decarbonylative cross-coupling of amides.

Authors:  Chengwei Liu; Michal Szostak
Journal:  Org Biomol Chem       Date:  2018-11-07       Impact factor: 3.876

5.  Palladium-Catalyzed Decarbonylative Difluoromethylation of Acid Chlorides at Room Temperature.

Authors:  Fei Pan; Gregory B Boursalian; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-16       Impact factor: 15.336

6.  Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.

Authors:  Anne Brennführer; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions.

Authors:  Nicolas Marion; Steven P Nolan
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

8.  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

9.  Decarbonylative organoboron cross-coupling of esters by nickel catalysis.

Authors:  Kei Muto; Junichiro Yamaguchi; Djamaladdin G Musaev; Kenichiro Itami
Journal:  Nat Commun       Date:  2015-06-29       Impact factor: 14.919

10.  Decarboxylative alkenylation.

Authors:  Jacob T Edwards; Rohan R Merchant; Kyle S McClymont; Kyle W Knouse; Tian Qin; Lara R Malins; Benjamin Vokits; Scott A Shaw; Deng-Hui Bao; Fu-Liang Wei; Ting Zhou; Martin D Eastgate; Phil S Baran
Journal:  Nature       Date:  2017-04-19       Impact factor: 49.962

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  3 in total

1.  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

2.  Evaluation of P-bridged biaryl phosphine ligands in palladium-catalysed Suzuki-Miyaura cross-coupling reactions.

Authors:  Jairus L Lamola; Paseka T Moshapo; Cedric W Holzapfel; Munaka Christopher Maumela
Journal:  RSC Adv       Date:  2021-08-05       Impact factor: 4.036

3.  Ni/Pd-catalyzed Suzuki-Miyaura cross-coupling of alcohols and aldehydes and C-N cross-coupling of nitro and amines via domino redox reactions: base-free, hydride acceptor-free.

Authors:  Milad Kazemnejadi; Rebin Omer Ahmed; Boshra Mahmoudi
Journal:  RSC Adv       Date:  2020-12-10       Impact factor: 4.036

  3 in total

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