Literature DB >> 26804615

Nickel-Catalyzed Activation of Acyl C-O Bonds of Methyl Esters.

Liana Hie1, Noah F Fine Nathel1, Xin Hong1, Yun-Fang Yang1, Kendall N Houk2, Neil K Garg3.   

Abstract

We report the first catalytic method for activating the acyl C-O bonds of methyl esters through an oxidative-addition process. The oxidative-addition adducts, formed using nickel catalysis, undergo in situ trapping to provide anilide products. DFT calculations are used to support the proposed reaction mechanism, to understand why decarbonylation does not occur competitively, and to elucidate the beneficial role of the substrate structure and the Al(OtBu)3 additive on the kinetics and thermodynamics of the reaction.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−O activation; density functional calculations; methyl esters; nickel catalysis; oxidative addition

Mesh：

Substances：

Year:  2016        PMID： 26804615      PMCID： PMC4821830          DOI： 10.1002/anie.201511486

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


  26 in total

1.  Direct and waste-free amidations and cycloadditions by organocatalytic activation of carboxylic acids at room temperature.

Authors:  Raed M Al-Zoubi; Olivier Marion; Dennis G Hall
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2.  Nucleophilic carbene and HOAt relay catalysis in an amide bond coupling: an orthogonal peptide bond forming reaction.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2007-10-11       Impact factor: 15.419

Review 3.  Metal-catalysed approaches to amide bond formation.

Authors:  C Liana Allen; Jonathan M J Williams
Journal:  Chem Soc Rev       Date:  2011-03-17       Impact factor: 54.564

4.  Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

Authors:  Mamoru Tobisu; Toshiaki Shimasaki; Naoto Chatani
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

6.  Mechanism of Ni-catalyzed selective C-O bond activation in cross-coupling of aryl esters.

Authors:  Zhe Li; Song-Lin Zhang; Yao Fu; Qing-Xiang Guo; Lei Liu
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419

7.  Functional-group-tolerant, nickel-catalyzed cross-coupling reaction for enantioselective construction of tertiary methyl-bearing stereocenters.

Authors:  Hanna M Wisniewska; Elizabeth C Swift; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-06-10       Impact factor: 15.419

Review 8.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

9.  Mechanistic study of chemoselectivity in Ni-catalyzed coupling reactions between azoles and aryl carboxylates.

Authors:  Qianqian Lu; Haizhu Yu; Yao Fu
Journal:  J Am Chem Soc       Date:  2014-05-27       Impact factor: 15.419

10.  Amide synthesis from alcohols and amines by the extrusion of dihydrogen.

Authors:  Lars Ulrik Nordstrøm; Henning Vogt; Robert Madsen
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419
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  16 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.  Breaking Amides using Nickel Catalysis.

Authors:  Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2017-01-06       Impact factor: 13.084

3.  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

4.  Nickel-Catalyzed Alkylation of Amide Derivatives.

Authors:  Bryan J Simmons; Nicholas A Weires; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2016-04-12       Impact factor: 13.084

5.  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

6.  Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination.

Authors:  Van T Tran; John A Gurak; Kin S Yang; Keary M Engle
Journal:  Nat Chem       Date:  2018-08-20       Impact factor: 24.427

7.  Pd-Catalyzed Acyl C-O Bond Activation for Selective Ring-Opening of α-Methylene-β-lactones with Amines.

Authors:  Christian A Malapit; Donald R Caldwell; Nicole Sassu; Samuel Milbin; Amy R Howell
Journal:  Org Lett       Date:  2017-04-04       Impact factor: 6.005

8.  Rapidly Activating Pd-Precatalyst for Suzuki-Miyaura and Buchwald-Hartwig Couplings of Aryl Esters.

Authors:  Amira H Dardir; Patrick R Melvin; Ryan M Davis; Nilay Hazari; Megan Mohadjer Beromi
Journal:  J Org Chem       Date:  2017-12-12       Impact factor: 4.354

9.  Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2.

Authors:  Jing Li; Martin J Lear; Yujiro Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-14       Impact factor: 15.336

10.  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
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