Literature DB >> 28294473

Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C-O and C-C Bond Activation.

Huifeng Yue1, Lin Guo1, Hsuan-Hung Liao1, Yunfei Cai1, Chen Zhu1, Magnus Rueping1,2.   

Abstract

An efficient nickel-catalyzed decarbonylative amination reaction of aryl and heteroaryl esters has been achieved for the first time. The new amination protocol allows the direct interconversion of esters and amides into the corresponding amines and represents a good alternative to classical rearrangements as well as cross coupling reactions.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amination; arenes; esters; nickel; reaction mechanisms

Year:  2017        PMID: 28294473     DOI: 10.1002/anie.201611819

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  20 in total

1.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

2.  Cross-Coupling and Related Reactions: Connecting Past Success to the Development of New Reactions for the Future.

Authors:  Louis-Charles Campeau; Nilay Hazari
Journal:  Organometallics       Date:  2018-11-27       Impact factor: 3.876

3.  Mechanism and Origins of Ligand-Controlled Stereoselectivity of Ni-Catalyzed Suzuki-Miyaura Coupling with Benzylic Esters: A Computational Study.

Authors:  Shuo-Qing Zhang; Buck L H Taylor; Chong-Lei Ji; Yuan Gao; Michael R Harris; Luke E Hanna; Elizabeth R Jarvo; K N Houk; Xin Hong
Journal:  J Am Chem Soc       Date:  2017-09-07       Impact factor: 15.419

4.  Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

Authors:  Timothy B Boit; Nicholas A Weires; Junyong Kim; Neil K Garg
Journal:  ACS Catal       Date:  2017-12-20       Impact factor: 13.084

5.  Mizoroki-Heck Cyclizations of Amide Derivatives for the Introduction of Quaternary Centers.

Authors:  Jose M Medina; Jesus Moreno; Sophie Racine; Shuaijing Du; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-03       Impact factor: 15.336

6.  Decarbonylative Sonogashira Cross-Coupling: Fruitful Marriage of Alkynes with Carboxylic Acid Electrophiles.

Authors:  Chengwei Liu; Michal Szostak
Journal:  Org Chem Front       Date:  2021-11-19       Impact factor: 5.456

7.  Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters.

Authors:  Christian A Malapit; Margarida Borrell; Michael W Milbauer; Conor E Brigham; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2020-03-24       Impact factor: 15.419

8.  Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of Aliphatic Amides on the Benchtop.

Authors:  Milauni M Mehta; Timothy B Boit; Jacob E Dander; Neil K Garg
Journal:  Org Lett       Date:  2019-10-17       Impact factor: 6.005

9.  A methylation platform of unconventional inert aryl electrophiles: trimethylboroxine as a universal methylating reagent.

Authors:  Boya Feng; Yudong Yang; Jingsong You
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

10.  Reductive Arylation of Amides via a Nickel-Catalyzed Suzuki-Miyaura-Coupling and Transfer-Hydrogenation Cascade.

Authors:  Timothy B Boit; Milauni M Mehta; Junyong Kim; Emma L Baker; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-30       Impact factor: 15.336

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