Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates

Dae-Yon Lee; John F Hartwig

doi:10.1021/ol050141b

Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates

Org Lett. 2005 Mar 17;7(6):1169-72. doi: 10.1021/ol050141b.

Authors

Dae-Yon Lee¹, John F Hartwig

Affiliation

¹ Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 6520-8107, USA.

PMID: 15760166
DOI: 10.1021/ol050141b

Abstract

[reaction: see text] We report that Zn[N(SiMe(3))(2)](2) is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe(3))(2), the combination of Zn[N(SiMe(3))(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(SiMe(3))(2)](2) and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amination
Ammonia / chemistry
Catalysis
Chemistry, Organic / methods*
Hydrocarbons, Halogenated / chemistry*
Mesylates / chemistry*
Molecular Structure
Palladium / chemistry*
Trimethylsilyl Compounds / chemistry*
Zinc / chemistry*

Substances

Hydrocarbons, Halogenated
Mesylates
Trimethylsilyl Compounds
Palladium
Ammonia
Zinc