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Switching between Copper‐Catalysis and Photocatalysis for Tunable Halofluoroalkylation and Hydrofluoroalkylation of 1,6‐Enynes toward 1‐Indenones
Author(s) -
Shen ZhengJia,
Wang ShiChao,
Hao WenJuan,
Yang ShiZhao,
Tu ShuJiang,
Jiang Bo
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900559
Subject(s) - chemistry , catalysis , halide , photocatalysis , copper , combinatorial chemistry , stereoselectivity , selectivity , organic chemistry
Tunable halofluoroalkylation and hydrofluoroalkylation of 1,6‐enynes were first reported by switching between copper‐catalysis and photocatalysis, leading to the atom‐economic and highly stereoselective protocols toward functionalized 1‐indenones with moderate to good yields. Copper‐catalysis enabled the concomitant incorporation of two important fluoroalkyl and halo functionalities into 1‐indenone skeleton, in which fluoroalkyl bromides were transformed into ( E )‐1‐indenones as a major stereoisomer while fluoroalkyl iodides oriented complete Z ‐selectivity to access ( Z )‐1‐indenones. Specifically, photocatalysis allowed hydrofluoroalkylation of 1,6‐enynes to access fluoroalkylated ( Z )‐1‐indenones under mild conditions, in which THF behaved as a hydrogen source. These two approaches feature remarkable compatibility with a wide variety of 1,6‐enynes and fluoroalkyl halides and excellent atomic utilization.