Literature DB >> 27717095

Functional Group Interconversion: Decarbonylative Borylation of Esters for the Synthesis of Organoboronates.

Lin Guo1, Magnus Rueping1,2.   

Abstract

A new and efficient nickel-catalyzed decarbonylative borylation reaction of carboxylic acid esters with bis(pinacolato)-diboron has been developed. This transformation allows access to structurally diverse aryl as well as alkenyl and alkyl boronate esters with high reactivity, broad substrate scope, and excellent functional-group tolerance. Further experiments show that this protocol can be carried out on a gram scale and applied to orthogonal synthetic strategies.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H borylation; C−O bond activation; decarbonylative cross-coupling; esters; nickel

Year:  2016        PMID: 27717095     DOI: 10.1002/chem.201604504

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

1.  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

2.  Heterogeneous Suzuki-Miyaura coupling of heteroaryl ester via chemoselective C(acyl)-O bond activation.

Authors:  Hongpeng Ma; Chaolumen Bai; Yong-Sheng Bao
Journal:  RSC Adv       Date:  2019-06-03       Impact factor: 4.036

3.  Nickel(0)-Catalyzed Decarbonylative Cross-Coupling of Aromatic Esters with Arylboronic Acids via Chelation Assistance.

Authors:  Zhenzhu Hu; Yuhang Wang; Peng Ma; Xiaqian Wu; Jianhui Wang
Journal:  ACS Omega       Date:  2022-06-13

4.  Suzuki-Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C-N and C-O bonds.

Authors:  Peng Lei; Guangrong Meng; Shicheng Shi; Yun Ling; Jie An; Roman Szostak; Michal Szostak
Journal:  Chem Sci       Date:  2017-08-01       Impact factor: 9.825

  4 in total

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