Alkylboronic pinacol
esters (APEs) are highly versatile reagents
in organic synthesis. However, the direct generation of alkyl radicals
from commonly used, bench-stable APEs has not been well explored.
In this communication, alkyl radical generation from APEs through
reaction with aminyl radicals is reported. The aminyl radicals are
readily generated by visible-light-induced homolytic cleavage of the
N–N bond in N-nitrosamines, and C radical
generation occurs through nucleohomolytic substitution at boron. As
an application, the highly efficient photochemical radical alkyloximation
of alkenes with APEs and N-nitrosamines under mild
conditions is presented. A wide range of primary, secondary, and tertiary
APEs engage in this transformation that is easily scaled up.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.