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 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.
Highlights
N-arylamines are an important structural motif present in an array of bioactive molecules including APIs and agrochemicals (Figure 1)
The methodology was further extended by combining with a dual-enzyme biocatalytic borrowing hydrogen cascade in one-pot, to allow for the conversion of a racemic alcohol to a chiral aniline
One frequently used Pd-catalysed transformation yet to be combined with biocatalysis is the Buchwald-Hartwig crosscoupling (BHA), which couples nucleophilic amines and aryl halides to afford anilines.[38,39,40,41]
Summary
Citation for published version (APA): Cosgrove, S., Thompson, M., Ahmed, S., Parmeggiani, F., & Turner, N. Onepot synthesis of chiral N arylamines by combining biocatalytic aminations with BuchwaldHartwig Narylation. Citing this paper Please note that where the full-text provided on Manchester Research Explorer is the Author Accepted Manuscript or Proof version this may differ from the final Published version. It is advised that you check and use the publisher's definitive version. General rights Copyright and moral rights for the publications made accessible in the Research Explorer are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. Supporting information for this article is given via a link at the end of the document
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