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

Paula RuizCastillo | Zendy; Donna G. Blackmond | Zendy; Stephen L. Buchwald | Zendy

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

Author(s) -

Paula RuizCastillo,

Donna G. Blackmond,

Stephen L. Buchwald

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja512903g

Subject(s) - chemistry , primary (astronomy) , rational design , ligand (biochemistry) , aryl , halide , combinatorial chemistry , kinetics , catalysis , aryl halide , computational chemistry , organic chemistry , nanotechnology , biochemistry , physics , materials science , receptor , alkyl , quantum mechanics , astronomy

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.

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