Photocatalytic Regioselective [2 + 2 + 1] Radical Annulation of Alkenes with tert-Butyl Nitrite and gem-Dihalides

Jiupeng Liu; Shuo Tang; Huayan Xu; Ruoyu Zhang; Jingjing Zhao; Puyu Zhang; Pan Li

doi:10.1021/acs.orglett.2c03635

Photocatalytic Regioselective [2 + 2 + 1] Radical Annulation of Alkenes with tert-Butyl Nitrite and gem-Dihalides

Org Lett. 2022 Dec 30;24(51):9366-9369. doi: 10.1021/acs.orglett.2c03635. Epub 2022 Dec 21.

Authors

Jiupeng Liu¹, Shuo Tang¹, Huayan Xu¹, Ruoyu Zhang¹, Jingjing Zhao¹, Puyu Zhang¹, Pan Li¹

Affiliation

¹ College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.

PMID: 36541616
DOI: 10.1021/acs.orglett.2c03635

Abstract

A visible-light photocatalytic regioselective [2 + 2 + 1] radical annulation reaction of alkenes, tert-butyl nitrite, and gem-dihalides has been developed. The protocol provides an efficient and practical approach to obtain isoxazolines in good yields under mild conditions. Significantly, gem-dihalides serve as C1 synthons, while cheap tert-butyl nitrite acts as an ideal "N-O" synthon.