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Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis

Paula Ruiz-Castillo, Donna G. Blackmond and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

P. Ruiz-Castillo, D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc., 2015, 137, 3085-3092.

DOI: 10.1021/ja512903g (free Supporting Information)


Abstract

Kinetics-based mechanistic analysis and rational design have led to the development of two biarylphosphine ligands that allow a Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines to proceed with excellent efficiency. The process enabled the coupling of a wide range of functionalized aryl and heteroaryl halides under mild conditions.

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Key Words

Buchwald-Hartwig Coupling


ID: J48-Y2015