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Rapid Dehydroxytrifluoromethoxylation of Alcohols.

ABSTRACT: 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.

SUBMITTER: Zhang W

PROVIDER: S-EPMC6123845 | biostudies-other | 2018 Jul

REPOSITORIES: biostudies-other

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Rapid Dehydroxytrifluoromethoxylation of Alcohols.

Zhang Wei W Chen Jia J Lin Jin-Hong JH Xiao Ji-Chang JC Gu Yu-Cheng YC

iScience 20180711

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 wi ...[more]

PMID: 30240641

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Dataset Information

Rapid Dehydroxytrifluoromethoxylation of Alcohols.

Publications

Rapid Dehydroxytrifluoromethoxylation of Alcohols.

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