Visible-Light-Induced Cascade Cyclization of 1-Acryloyl-2-cyanoindole: Access of Difluoroalkylated Pyrrolo[1,2- a]indolediones

Jinwei Yuan; Lu Shen; Na Guo; Yanli Yin; Pengyuan Yang; Liangru Yang; Yongmei Xiao; Shouren Zhang

doi:10.1021/acs.joc.3c02183

Visible-Light-Induced Cascade Cyclization of 1-Acryloyl-2-cyanoindole: Access of Difluoroalkylated Pyrrolo[1,2- a]indolediones

J Org Chem. 2023 Dec 1;88(23):16598-16608. doi: 10.1021/acs.joc.3c02183. Epub 2023 Nov 10.

Authors

Jinwei Yuan¹, Lu Shen¹, Na Guo², Yanli Yin², Pengyuan Yang¹, Liangru Yang¹, Yongmei Xiao¹, Shouren Zhang³

Affiliations

¹ School of Chemistry & Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China.
² College of Advanced Interdisciplinary Science and Technology, Henan University of Technology, Zhengzhou 450001, P. R. China.
³ Henan Key Laboratory of Nanocomposites and Applications, Institute of Nanostructured Functional Materials, Huanghe Science and Technology College, Zhengzhou 450006, P. R. China.

PMID: 37948397
DOI: 10.1021/acs.joc.3c02183

Abstract

An effective method for accessing diverse difluoroalkylated pyrrolo[1,2-a]indolediones via visible-light-induced PhI(OAc)₂-promoted cascade difluoroalkylation/cyclization reaction under mild conditions has been established. This method is noteworthy for its use of DMSO-H₂O as a green medium at room temperature and avoidance of photocatalysts. The reactions are straightforward to execute and convenient to expand on, provide good to excellent yields, and have good functional group tolerance.