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

Sunwoo Lee, Morten Jørgensen and John F. Hartwig*

*Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, Email: jhartwigberkeley.edu

S. Lee, M. Jørgensen, J. F. Hartwig, Org. Lett., 2001, 3, 2729-2732.

DOI: 10.1021/ol016333y

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Abstract

The use of lithium bis(trimethylsilyl)amide (LiN(SiMe₃)₂) enables a simple, palladium-catalyzed conversion of aryl halides to the parent anilines. The reaction is catalyzed by Pd(dba)₂ and P(t-Bu)₃ and can be run with as little as 0.2 mol % of catalyst.

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Palladium-Catalyzed Coupling of Ammonia with Aryl Chlorides, Bromides, Iodides, and Sulfonates: A General Method for the Preparation of Primary Arylamines

G. D. Vo, J. F. Hartwig, J. Am. Chem. Soc., 2009, 131, 11049-11061.

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Key Words

Buchwald-Hartwig Coupling, Anilines

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ID: J54-Y2020