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Letter

Zinc Trimethylsilylamide as a Mild Ammonia Equivalent and Base for the Amination of Aryl Halides and Triflates

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Dae-Yon Lee and John F. Hartwig*

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 6520-8107

Org. Lett., 2005, 7 (6), pp 1169–1172

DOI: 10.1021/ol050141b

Publication Date (Web): February 24, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, john.hartwig@yale.edu

Abstract

We report that Zn[N(SiMe₃)₂]₂ is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe₃)₂, the combination of Zn[N(SiMe₃)₂]₂ and LiCl coupled with aryl halides and triflates containing base-sensitive functionality in high yields. In addition, aryl bromides coupled with aryl and alkylamines with the combination of Zn[N(SiMe₃)₂]₂ and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester.

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Published In Issue March 17, 2005
Received January 21, 2005

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Letter

Zinc Trimethylsilylamide as a Mild Ammonia Equivalent and Base for the Amination of Aryl Halides and Triflates

Abstract

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Recommend & Share

Related Content

Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides Palladium-Catalyzed Coupling of Ammonia and Lithium Amide with Aryl Halides

Palladium-Catalyzed Synthesis of Arylamines from Aryl Halides and Lithium Bis(trimethylsilyl)amide as an Ammonia Equivalent

Selective Palladium-Catalyzed Arylation of Ammonia: Synthesis of Anilines as Well as Symmetrical and Unsymmetrical Di- and Triarylamines

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