One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation.

Cosgrove

doi:10.1002/anie.202006246

One-Pot Synthesis of Chiral N-Arylamines by Combining Biocatalytic Aminations with Buchwald-Hartwig N-Arylation.

Cosgrove

Authors

Sebastian Cosgrove s.cosgrove@keele.ac.uk

Abstract

The combination of biocatalysis and chemo-catalysis increasingly offers chemists access to more diverse chemical architectures. Here, we describe the combination of a toolbox of chiral-amine-producing biocatalysts with a Buchwald-Hartwig cross-coupling reaction, affording a variety of a-chiral aniline derivatives. The use of a surfactant allowed reactions to be performed sequentially in the same flask, preventing the palladium catalyst from being inhibited by the high concentrations of ammonia, salts, or buffers present in the aqueous media in most cases. The methodology was further extended by combining with a dual-enzyme biocatalytic hydrogen-borrowing cascade in one pot to allow for the conversion of a racemic alcohol to a chiral aniline.

Acceptance Date	Jul 3, 2020
Publication Date	Oct 5, 2020
Journal	Angewandte Chemie
Print ISSN	0044-8249
Publisher	Wiley
Pages	18156 - 18160
DOI	https://doi.org/10.1002/anie.202006246
Keywords	amines; biocatalysis; chemo-enzymatic synthesis; enzymes; palladium catalysis
Publisher URL	https://onlinelibrary.wiley.com/doi/10.1002/anie.202006246