DOI: 10.1021/acs.joc.6c01469 ISSN: 0022-3263

Selectfluor-Mediated Radical Cyclization of N -Arylbicyclo[1.1.0]butane-1-carboxamides with Diaryldiselenides

Yuze Lin, Yina Liu, Gang Yang, Yadong Feng, Xiuling Cui

Abstract

Herein, we report a Selectfluor-mediated radical cascade cyclization of bicyclo[1.1.0]butanes (BCBs) with diaryl selenides through strain-promoted C–C σ-bond cleavage. This protocol provides a facile and efficient approach to selenium-decorated 3-spirocyclobutyl oxindoles in up to 99% yield for 30 examples. Moreover, the reaction is readily scalable to the gram scale, demonstrating its practical applicability. This protocol features a broad scope of substrate, peroxide-free, rapid, mild, and environmentally benign conditions, with excellent tolerance of broad functional groups.