Literature DB >> 11975563

Nickel(0)/dihydroimidazol-2-ylidene complex catalyzed coupling of aryl chlorides and amines.

Christophe Desmarets1, Raphaël Schneider, Yves Fort.   

Abstract

A general and simple nickel-catalyzed coupling of aryl chlorides and amines is reported. The scope and limitations of the coupling process using Ni(0), 1,3-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene, and NaO-t-Bu as base were investigated. Secondary cyclic and acyclic amines and anilines provided the arylamine coupling products in good to excellent yields. Compared to palladium-catalyzed aminations, this procedure offers an alternative route to N-substituted anilines starting from readily available aryl chlorides.

Entities:  

Year:  2002        PMID： 11975563     DOI： 10.1021/jo016352l

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 in total

Review 1.  Nickel-catalyzed cross-couplings involving carbon-oxygen bonds.

Authors:  Brad M Rosen; Kyle W Quasdorf; Daniella A Wilson; Na Zhang; Ana-Maria Resmerita; Neil K Garg; Virgil Percec
Journal:  Chem Rev       Date:  2010-12-06       Impact factor: 60.622

2.  Photoinduced Cleavage of N-N Bonds of Aromatic Hydrazines and Hydrazides by Visible Light.

Authors:  Mingzhao Zhu; Nan Zheng
Journal:  Synthesis (Stuttg)       Date:  2011-06-21       Impact factor: 3.157

3.  Transition-metal free umpolung carbon-nitrogen vs. carbon-chlorine bond formation.

Authors:  John J Sirois; Brenton DeBoef
Journal:  Tetrahedron Lett       Date:  2015-10-07       Impact factor: 2.415

4.  Facile N-arylation of amines and sulfonamides and o-arylation of phenols and arenecarboxylic acids.

Authors:  Zhijian Liu; Richard C Larock
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

5.  Nickel-catalyzed amination of aryl chlorides with ammonia or ammonium salts.

Authors:  Rebecca A Green; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-25       Impact factor: 15.336

6.  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

7.  Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst.

Authors:  Liana Hie; Stephen D Ramgren; Tehetena Mesganaw; Neil K Garg
Journal:  Org Lett       Date:  2012-07-31       Impact factor: 6.005

8.  Controlling first-row catalysts: amination of aryl and heteroaryl chlorides and bromides with primary aliphatic amines catalyzed by a BINAP-ligated single-component Ni(0) complex.

Authors:  Shaozhong Ge; Rebecca A Green; John F Hartwig
Journal:  J Am Chem Soc       Date:  2014-01-21       Impact factor: 15.419

9.  Iron Oxide-Cobalt Nanocatalyst for O-tert-Boc Protection and O-Arylation of Phenols.

Authors:  Vilas B Gade; Anandarup Goswami; Rajender S Varma; Sharad N Shelke; Manoj B Gawande
Journal:  Nanomaterials (Basel)       Date:  2018-04-17       Impact factor: 5.076

10.  Nickel-Catalyzed Amination of Aryl Chlorides and Sulfamates in 2-Methyl-THF.

Authors:  Noah F Fine Nathel; Junyong Kim; Liana Hie; Xingyu Jiang; Neil K Garg
Journal:  ACS Catal       Date:  2014-08-20       Impact factor: 13.084
  10 in total

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