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Chan-Lam Amination of Benzylic Secondary and Tertiary Boronic Esters

preprint
revised on 30.03.2021, 09:49 and posted on 30.03.2021, 13:24 by James D. Grayson, Francesca M. Dennis, Craig Robertson, Benjamin Partridge
The Cu-catalysed coupling of arylboronic acids with amines, known as the Chan-Lam reaction, is used widely to prepare aryl amines. In contrast, alkyl variants of this reaction, while highly desirable, are underdeveloped. Herein, we report a Chan-Lam coupling reaction of benzylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition metal-mediated transformation of a tertiary alkylboron reagent. The method is operationally simple and tolerates a broad range of functional groups. Initial investigation into the reaction mechanism suggests that transmetallation from B to Cu occurs through a single electron, rather than a two-electron process.

Funding

Cu-Catalysed Amination of Alkylboronic Esters

Engineering and Physical Sciences Research Council

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History

Email Address of Submitting Author

b.m.partridge@sheffield.ac.uk

Institution

University of Sheffield

Country

UK

ORCID For Submitting Author

0000-0002-8550-9994

Declaration of Conflict of Interest

no conflict of interest

Version Notes

Two extra experiments were added to the manuscript and SI, and some minor edits to the text were made.

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