Literature DB >> 32125073

Nickel or Palladium-Catalyzed Decarbonylative Transformations of Carboxylic Acid Derivatives.

Zhenhua Wang1, Xiu Wang1, Yasushi Nishihara2.   

Abstract

Carboxylic acid derivatives containing acyl halides, anhydrides, esters, amides and acyl nitriles are highly appealing electrophiles in transition-metal-catalyzed carbon-carbon bond-forming reactions due to their ready availability and low cost, which can provide divergent transformations of carboxylic acids into other value-added products. In this Minireview, we focus on the recent advances of decarbonylative transformations of carboxylic acid derivatives in carbon-carbon bond formations using Ni or Pd catalysts. A series of reaction types, product classifications and reaction pathways are presented herein, which show the advantageous features of carboxylic acid derivatives as alternative to aryl or alkyl halides in terms of reactivity and compatibility. The well-accepted mechanism of nickel- or palladium-catalyzed decarbonylative transformations involves initial oxidative addition of carboxylic acid derivatives, followed by decarbonylation or transmetalation (or insertion), and reductive elimination to generate the products, thereby regenerating the catalysts.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbon-carbon bond formation; carboxylic acid derivatives; decarbonylation; nickel; palladium

Year:  2020        PMID: 32125073     DOI: 10.1002/asia.202000117

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  6 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.  Decarbonylative Fluoroalkylation at Palladium(II): From Fundamental Organometallic Studies to Catalysis.

Authors:  Naish Lalloo; Christian A Malapit; S Maryamdokht Taimoory; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2021-10-28       Impact factor: 15.419

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.  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

5.  Silver Catalyzed Decarbonylative [3 + 2] Cycloaddition of Cyclobutenediones and Formamides.

Authors:  Pengcheng Wang; Ruirui Yu; Sajjad Ali; Zhengshen Wang; Zhigang Liu; Jinming Gao; Huaiji Zheng
Journal:  Molecules       Date:  2021-05-17       Impact factor: 4.411

6.  Efficient cleavage of tertiary amide bonds via radical-polar crossover using a copper(ii) bromide/Selectfluor hybrid system.

Authors:  Zhe Wang; Akira Matsumoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-10-14       Impact factor: 9.825

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.