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

Raghunath Reddy Anugu; John R Falck

doi:10.1039/d2sc00758d

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

Chem Sci. 2022 Apr 5;13(17):4821-4827. doi: 10.1039/d2sc00758d. eCollection 2022 May 4.

Authors

Raghunath Reddy Anugu¹, John R Falck¹

Affiliation

¹ Chemistry Division, Biochemistry Dept., Pharmacology Dept., University of Texas Southwestern Medical Center Dallas TX 75390 USA anugu.raghunathreddy@utsouthwestern.edu.

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.