Chan–Lam Amination of Secondary and Tertiary Benzylic Boronic Esters

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 r...

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Veröffentlicht in:Journal of organic chemistry 2021-07, Vol.86 (14), p.9883-9897
Hauptverfasser: Grayson, James D, Dennis, Francesca M, Robertson, Craig C, Partridge, Benjamin M
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00976