Jia-ying Xue,Jia-hui Shi,Yuan Yao,Wei-en Xie,Yong Zou,Ming Yan,Xue-jing Zhang

Organic Letters

DOI: 10.1021/acs.orglett.6c00234

Abstract

We report a skeletal editing strategy based on DNA-encoded nitroarenes for the direct conversion of benzene cores into valuable 3H-azepine scaffolds. This transformation is efficiently promoted by visible light in the presence of P(Oi-Pr)3, which serves as a reductant to generate reactive nitrene intermediates from the nitro group. Demonstrating broad substrate scope with applicability to pharmaceutical molecules, this protocol offers an efficient and versatile route to DNA-encoded 3H-azepine derivatives. It thus establishes a robust platform for skeletal diversification in DNA-encoded library synthesis.