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

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.

SUBMITTER: Anugu RR

PROVIDER: S-EPMC9067586 | biostudies-literature | 2022 May

REPOSITORIES: biostudies-literature

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

Anugu Raghunath Reddy RR Falck John R JR

Chemical science 20220405 17

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. ...[more]

PMID: 35655896

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