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Rational ligand design for the arylation of hindered primary amines guided by reaction progress kinetic analysis.

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

SUBMITTER: Ruiz-Castillo P 

PROVIDER: S-EPMC4379963 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

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Rational ligand design for the arylation of hindered primary amines guided by reaction progress kinetic analysis.

Ruiz-Castillo Paula P   Blackmond Donna G DG   Buchwald Stephen L SL  

Journal of the American Chemical Society 20150218 8

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

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