Grayson, J.D., Dennis, F.M., Robertson, C.C. et al. (1 more author) (2021) Chan–Lam amination of secondary and tertiary benzylic boronic esters. The Journal of Organic Chemistry, 86 (14). pp. 9883-9897. ISSN 0022-3263
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2021 The Authors. Published by American Chemical Society. Article available under the terms of the CC-BY licence (https://creativecommons.org/licenses/by/4.0/). |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Funding Information: | Funder Grant number The Royal Society RSG\R1\180065 Engineering and Physical Science Research Council EP/T009292/1 |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 08 Jul 2021 12:56 |
Last Modified: | 21 Feb 2022 11:35 |
Status: | Published |
Publisher: | American Chemical Society (ACS) |
Refereed: | Yes |
Identification Number: | 10.1021/acs.joc.1c00976 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:175621 |