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An Efficient Silane-Promoted Nickel-Catalyzed Amination of Aryl and Heteroaryl Chlorides

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Georg Manolikakes, Andrei Gavryushin, and Paul Knochel*

Department Chemie und Biochemie, Ludwig-Maximilians-Universität, Butenandtstrasse 5-13, 81377 Munich, Germany

J. Org. Chem., 2008, 73 (4), pp 1429–1434

DOI: 10.1021/jo702219f

Publication Date (Web): January 23, 2008

Section:

Benzene, Its Derivatives, and Condensed Benzenoid Compounds

Abstract

A new silane-promoted nickel-catalyzed amination of aryl chlorides with 0.5 mol % of Ni(acac)₂, 1 mol % of 3,5,6,8-tetrabromo-1,10-phenanthroline, and polymethylhydrosiloxane was developed. A broad range of aryl and heteroaryl chlorides can be coupled with secondary amines and anilines to give the desired (het)arylamines in good to excellent yields. The reaction is sensitive to the nature and amount of the silane promoter.

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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Yuki Nakamura, Laurean Ilies, and Eiichi Nakamura
Organic Letters2011 13 (22), 5998-6001
- Iron-Catalyzed Oxidative Monoarylation of Primary Amines with Organozinc Reagents
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  Organic Letters2011 13 (22), 5998-6001
  The reaction of a primary zinc amide with a diorganozinc reagent gives a secondary amine in the presence of Fe(acac)3 as a catalyst and 1,2-dichloroisobutane (DCIB) as an oxidant. Halogen groups such as F, Cl, Br, and I are tolerated well. The dichloride ...
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N-Heterocyclic Carbene Bound Nickel(I) Complexes and Their Roles in Catalysis
Kainan Zhang, Martin Conda-Sheridan, Shayna R. Cooke, and Janis Louie
Organometallics2011 Article ASAP
- N-Heterocyclic Carbene Bound Nickel(I) Complexes and Their Roles in Catalysis
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  Organometallics2011 Article ASAP
  The new paramagnetic complexes NiI(IMes)2X (IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene) were prepared from the reaction of Ni(IMes)2 with aryl halides. Products that would arise from oxidative addition were not observed. In contrast, NiII(...
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Transition-Metal-Free Electrophilic Amination between Aryl Grignard Reagents and N-Chloroamines
Takuji Hatakeyama, Yuya Yoshimoto, Sujit K. Ghorai and Masaharu Nakamura
Organic Letters2010 12 (7), 1516-1519
- Transition-Metal-Free Electrophilic Amination between Aryl Grignard Reagents and N-Chloroamines
  Takuji Hatakeyama, Yuya Yoshimoto, Sujit K. Ghorai and Masaharu Nakamura
  Organic Letters2010 12 (7), 1516-1519
  In the presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) as an additive, easily prepared and handled N-chloroamines react with aryl Grignard reagents to give a variety of arylamines in good to excellent yields. Functional groups such as ester and ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links