Synthesis 2020; 52(24): 3865-3873
DOI: 10.1055/s-0040-1707863
special topic
© Georg Thieme Verlag Stuttgart · New York

Iridium(III)-Catalyzed Difluoroalkylation–Bicyclization of 1,7-Enynes toward Benzo[a]fluoren-5-ones under Visible-Light Photoredox Conditions

Authors

  • Min-Hua Huang

    a   School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China
    b   Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 210009, Jiangsu, P. R. of China   Email: jiangchem@jsnu.edu.cn
  • Wen-Juan Hao

    a   School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China
  • Bo Jiang

    a   School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. of China

We are grateful for financial support from the National Natural Science Foundation of China (NSFC) (Grant No. 21971090).
Further Information

Publication History

Received: 05 April 2020

Accepted after revision: 07 May 2020

Publication Date:
16 June 2020 (online)


Graphical Abstract

Preview

Published as part of the Special Topic Recent Advances in Metal-Catalyzed Ring Construction

Abstract

A new visible-light-induced Ir(III)-catalyzed difluoroalkylation–bicyclization of 1,7-enynes with ethyl 2-bromo-2,2-difluoroacetate (BrCF2CO2Et) is described, furnishing a wide range of difluoromethyl-containing benzo[a]fluoren-5-ones in good to excellent yields. The reaction is operationally simple, proceeds with high efficiency under mild conditions, and shows excellent functional group compatibility.

Supporting Information