Rational and Predictable Chemoselective Synthesis of Oligoamines via Buchwald-Hartwig Amination of (Hetero)Aryl Chlorides Employing Mor-DalPhos

Bennett J. Tardiff, Robert McDonald, Michael J. Ferguson, and Mark Stradiotto*

*Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. Box 15000, Halifax, Nova Scotia, Canada B3H 4R2, Email: mark.stradiottodal.ca

B. J. Tardiff, R. McDonald, M. J. Ferguson, M. Stradiotto, J. Org. Chem., 2012, 77, 1056-1071.

DOI: 10.1021/jo202358p

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Abstract

The use of [Pd(cinnamyl)Cl]₂ in the presence of N-(2-(di(1-adamantyl)phosphino)phenyl)morpholine (Mor-DalPhos) enables a selective Buchwald-Hartwig monoamination of aryl chlorides with diamines. Competition reactions established a relative preference of this catalyst system for amine coupling partners favouring linear primary alkylamines and imines.

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Key Words

Buchwald-Hartwig Coupling

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ID: J42-Y2012-0110