Journal
ISCIENCE
Volume 5, Issue -, Pages 110-+Publisher
CELL PRESS
DOI: 10.1016/j.isci.2018.07.004
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Funding
- National Basic Research Program of China [2015CB931903]
- National Natural Science Foundation [21421002, 21472222, 21502214, 21672242]
- Chinese Academy of Sciences [XDA02020105, XDA02020106]
- Key Research Program of Frontier Sciences (CAS) [QYZDJ-SSW-SLH049]
- Syngenta PhD Fellowship
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The CF3O functional group is a unique fluorinated group that has received a great deal of attention in medicinal chemistry and agrochemistry. However, trifluoromethoxylation of substrates remains a challenging task. Herein we describe the dehydroxytrifluoromethoxylation of alcohols promoted by a R3P/ICH2CH2I(R3P = Ph3P or Ph2PCH=CH2) system in DMF. P-I halogen bonding drives the reaction of R3P with ICH2CH2I in DMF to generate iodophosphonium salt (R3P+I I-) and a Vilsmeier-Haack-type intermediate, both of which could effectively activate alcohols, thus enabling a fast (15 min) trifluoromethoxylation reaction. A wide substrate scope and a high level of functional group tolerance were observed.
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