Literature DB >> 30079273

Stable, Well-Defined Nickel(0) Catalysts for Catalytic C-C and C-N Bond Formation.

Alex J Nett1, Santiago Cañellas1, Yuki Higuchi1, Michael T Robo1, Jeanne M Kochkodan1, M Taylor Haynes1, Jeff W Kampf1, John Montgomery1.   

Abstract

The synthesis and catalytic activity of several classes of NHC-n class="Chemical">Ni(0) pre-catalysts stabilized by electron-withdrawing alkenes are described. Variations in the structure of fumarate and acrylate ligands modulate the reactivity and stability of the NHC-Ni(0) pre-catalysts and lead to practical and versatile catalysts for a variety of transformations. The catalytic activity and efficiency of representative members of this class of catalysts have been evaluated in reductive couplings of aldehydes and alkynes and in N-arylations of aryl chlorides.

Entities:  

Keywords:  N-heterocyclic carbenes; amination; catalysis; precatalyst; reductive coupling

Year:  2018        PMID: 30079273      PMCID: PMC6071431          DOI: 10.1021/acscatal.8b02187

Source DB:  PubMed          Journal:  ACS Catal            Impact factor:   13.084


  24 in total

1.  Rapid and selective catalytic oxidation of secondary alcohols at room temperature by using (N-heterocyclic carbene)-ni(0) systems.

Authors:  Christophe Berini; Ole H Winkelmann; Jennifer Otten; David A Vicic; Oscar Navarro
Journal:  Chemistry       Date:  2010-06-18       Impact factor: 5.236

2.  Deoxygenative C-C Bond-Forming Processes via a Net Four-Electron Reductive Coupling.

Authors:  David P Todd; Benjamin B Thompson; Alex J Nett; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-10-05       Impact factor: 15.419

3.  A two-coordinate nickel imido complex that effects C−H amination.

Authors:  Carl A Laskowski; Alexander J M Miller; Gregory L Hillhouse; Thomas R Cundari
Journal:  J Am Chem Soc       Date:  2011-02-02       Impact factor: 15.419

4.  Development of a Modular Synthetic Route to (+)-Pleuromutilin, (+)-12-epi-Mutilins, and Related Structures.

Authors:  Mingshuo Zeng; Stephen K Murphy; Seth B Herzon
Journal:  J Am Chem Soc       Date:  2017-11-02       Impact factor: 15.419

5.  Highly Active Nickel Catalysts for C-H Functionalization Identified through Analysis of Off-Cycle Intermediates.

Authors:  Alex J Nett; Wanxiang Zhao; Paul M Zimmerman; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

6.  A modular, air-stable nickel precatalyst.

Authors:  Jason D Shields; Erin E Gray; Abigail G Doyle
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.005

7.  Development of an air-stable nickel precatalyst for the amination of aryl chlorides, sulfamates, mesylates, and triflates.

Authors:  Nathaniel H Park; Georgiy Teverovskiy; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-11-27       Impact factor: 6.005

8.  Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes.

Authors:  Eric A Standley; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2013-01-14       Impact factor: 15.419

9.  Linear-selective hydroarylation of unactivated terminal and internal olefins with trifluoromethyl-substituted arenes.

Authors:  Joseph S Bair; York Schramm; Alexey G Sergeev; Eric Clot; Odile Eisenstein; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-09-15       Impact factor: 15.419

10.  Anti-Markovnikov hydroheteroarylation of unactivated alkenes with indoles, pyrroles, benzofurans, and furans catalyzed by a nickel-N-heterocyclic carbene system.

Authors:  York Schramm; Makoto Takeuchi; Kazuhiko Semba; Yoshiaki Nakao; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-09-16       Impact factor: 15.419

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  5 in total

1.  Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

Authors:  Santiago Cañellas; John Montgomery; Miquel À Pericàs
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Using JPP to Identify Ni Bidentate Phosphine Complexes In Situ.

Authors:  Matthew D Hannigan; Anne J McNeil; Paul M Zimmerman
Journal:  Inorg Chem       Date:  2021-08-18       Impact factor: 5.165

3.  NHC-Ni(II)-catalyzed cyclopropene-isocyanide [5 + 1] benzannulation.

Authors:  Jian-Qiang Huang; Meng Yu; Xuefeng Yong; Chun-Yu Ho
Journal:  Nat Commun       Date:  2022-07-16       Impact factor: 17.694

4.  Stereoselective synthesis of pentasubstituted 1,3-dienes via Ni-catalyzed reductive coupling of unsymmetrical internal alkynes.

Authors:  Zhijun Zhou; Jiachang Chen; Herong Chen; Wangqing Kong
Journal:  Chem Sci       Date:  2020-09-10       Impact factor: 9.825

5.  Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol.

Authors:  Herong Chen; Zhijun Zhou; Wangqing Kong
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.825

  5 in total

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