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One‐Pot Synthesis of Chiral N ‐Arylamines by Combining Biocatalytic Aminations with Buchwald–Hartwig N ‐Arylation
Author(s) -
Cosgrove Sebastian C.,
Thompson Matthew P.,
Ahmed Syed T.,
Parmeggiani Fabio,
Turner Nicholas J.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006246
Subject(s) - aniline , chemistry , biocatalysis , catalysis , amination , amine gas treating , combinatorial chemistry , organic chemistry , enantioselective synthesis , palladium , ionic liquid
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 α‐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.