Synlett 2021; 32(15): 1547-1550
DOI: 10.1055/s-0040-1707170
cluster
Modern Nickel-Catalyzed Reactions

Ligand-Free Nickel-Catalyzed Reductive Allylic Defluorinative Cross-Coupling of α-Trifluoromethyl Alkenes with Epoxides

Zhiyang Lin
a   Hefei National Laboratory for Physical Science at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
,
Yun Lan
a   Hefei National Laboratory for Physical Science at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
,
Chuan Wang
a   Hefei National Laboratory for Physical Science at the Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
b   Center for Excellence in Molecular Synthesis of CAS, Hefei, Anhui 230026, P. R. of China
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (Grant No. 21772183), the Fundamental Research Funds for the Central Universities (WK2060190086), ‘1000-Youth Talents Plan’ start-up funding, and by the University of Science and Technology of China.


Abstract

We report a reductive allylic defluorinative reaction of α-trifluoromethyl alkenes with terminal epoxides, which consists of an iodide-mediated regioselective ring opening and a nickel-catalyzed radical-type cross-coupling, providing diverse tertiary gem-difluorobishomoallylic alcohols in moderate to high yields. Notably, this reaction is conducted under mild conditions and requires no external ligand or proton donor.

Supporting Information



Publication History

Received: 05 May 2020

Accepted: 01 June 2020

Article published online:
01 July 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany