Site-selective amination and/or nitrilation via metal-free C(sp2)–C(sp3) cleavage of benzylic and allylic alcohols?

Chemical Science Pub Date: 2022-04-05 DOI: 10.1039/D2SC00758D

Abstract

Benzylic/allylic alcohols are converted via site-selective C(sp2)–C(sp3) cleavage to value-added nitrogenous motifs, viz., anilines and/or nitriles as well as N-heterocycles, utilizing commercial hydroxylamine-O-sulfonic acid (HOSA) and Et3N in an operationally simple, one-pot process. Notably, cyclic benzylic/allylic alcohols undergo bis-functionalization with attendant increases in architectural complexity and step-economy.

Graphical abstract: Site-selective amination and/or nitrilation via metal-free C(sp2)–C(sp3) cleavage of benzylic and allylic alcohols
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