Abstract
We report a Chan-Lam coupling reaction of benzylic and allylic 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. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process.
Highlights
We report a Chan−Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products
Because of the versatility of organoboron reagents, we are interested in developing an alkyl variant of the Chan−Lam reaction (Scheme 1)
This reaction has been studied in detail for Scheme 1
Summary
Partridge − Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom; orcid.org/ 0000-0002-8550-9994; Email: b.m.partridge@ sheffield.ac.uk. Grayson − Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom. Dennis − Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom. Robertson − Department of Chemistry, University of Sheffield, Sheffield S3 7HF, United Kingdom.
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