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The Photoinduced Metal‐Free Hydrotrifluoromethylation of Vinyl Phosphonates or Phosphine Oxides
Author(s) -
Yao Qiuli,
Ren Linjing,
Xiang Dan,
Li Kexin,
Yan Boyu,
Ran Maogang,
He Jiaxin,
Zhao Liang
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901366
Subject(s) - chemistry , phosphine , radical , catalysis , photochemistry , hydrogen peroxide , phosphine oxide , solvent , acetone , ultraviolet light , metal , oxide , yield (engineering) , organic chemistry , materials science , metallurgy
We describe a simple and metal‐free photochemical strategy for the direct hydrotrifluoromethylation of vinyl phosphonates or phosphine oxides by sodium triflinate under ultraviolet or visible light irradiation. Acetone and diacetyl were used as radical initiators to generate CF 3 radicals that were efficiently added to vinyl phosphonates or phosphine oxide to yield β‐trifluoromethylated phosphorus compounds without the use of any catalyst. A broad scope of substrates scope is demonstrated in moderate to excellent yields. Mechanistic experiments were performed to study the source of hydrogen; the results indicate that H 2 O in the solvent or additive is the primary hydrogen source.