Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates.
[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.
Lee
Dae-Yon
DY
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 6520-8107, USA.
Hartwig
John F
JF
D000586:Amination; D000641:Ammonia / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*; D015032:Zinc / Q000737:chemistry*
D006846:Hydrocarbons, Halogenated; D008698:Mesylates; D014297:Trimethylsilyl Compounds; D010165:Palladium; D000641:Ammonia; D015032:Zinc