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Rapid and efficient access to secondary arylmethylamines.

ABSTRACT: Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have been designed, based on the use of an aminobiphenyl palladium precatalyst, to couple these trifluoroborates efficiently with aryl bromides. This strategy offers a new way to access biologically relevant motifs and allows, with the previously developed methods, access to all three classes of aminomethylarenes.

SUBMITTER: Fleury-Bregeot N

PROVIDER: S-EPMC3415697 | biostudies-literature | 2012 Jul

REPOSITORIES: biostudies-literature

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Rapid and efficient access to secondary arylmethylamines.

Fleury-Brégeot Nicolas N Raushel Jessica J Sandrock Deidre L DL Dreher Spencer D SD Molander Gary A GA

Chemistry (Weinheim an der Bergstrasse, Germany) 20120705 31

Ammoniomethyl trifluoroborates are very powerful reagents that can be used to access biologically relevant aryl- and heteroaryl-methylamine motifs via Suzuki-Miyaura cross-couplings. Until now, this method was limited to the production of tertiary and primary amines. The synthesis of a large array of secondary ammoniomethyltrifluoroborates has been achieved through a one step nucleophilic substitution reaction on the potassium bromomethyltrifluoroborate. Smooth cross-coupling conditions have bee ...[more]

PMID: 22767518

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