Catalyst- and additive-free cascade radical addition/cyclization of N-arylacrylamides with trifluoropyruvates

Yongbo Tan; Huawen Huang

doi:10.1039/d3cc04542k

Catalyst- and additive-free cascade radical addition/cyclization of N-arylacrylamides with trifluoropyruvates

Chem Commun (Camb). 2023 Nov 9;59(90):13462-13465. doi: 10.1039/d3cc04542k.

Authors

Yongbo Tan¹, Huawen Huang^{1

2}

Affiliations

¹ Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China. hwhuang@xtu.edu.cn.
² School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007, P. R. China.

PMID: 37877176
DOI: 10.1039/d3cc04542k

Abstract

Herein, we introduce a photocatalyst- and additive-free method for the preparation of valuable 3,3-disubstituted oxindoles bearing trifluoromethyl alcohol moieties from readily available acrylamides and cheap trifluoropyruvates. The excited trifluoropyruvates under ultraviolet-light irradiation react efficiently with acrylamides delivering a variety of trifluoromethyl oxindoles with broad functional group tolerance and moderate to good yields. This protocol features mild reaction conditions, simple operation and ready scalability.