Hydroxytrifluoromethylation of Alkenes Using Fluoroform-Derived CuCF3
Xinkan Yang1, Lisi He1, Gavin Chit Tsui1
1Department of Chemistry, The Chinese University of Hong Kong , Shatin, New Territories, Hong Kong SAR.
Organic Letters
|April 26, 2017
Summary
This study introduces a new method for hydroxytrifluoromethylation of alkenes using a copper-based reagent derived from fluoroform. This process efficiently synthesizes valuable trifluoromethyl alcohols from simple alkenes.
Area of Science:
- Organic Chemistry
- Organometallic Chemistry
- Fluorine Chemistry
Background:
- Trifluoromethylated organic compounds are crucial in pharmaceuticals and materials science.
- Direct trifluoromethylation methods often require expensive or hazardous reagents.
- Fluoroform (CF3H) is an abundant industrial byproduct, making it an attractive CF3 source.
Purpose of the Study:
- To develop an efficient method for hydroxytrifluoromethylation of alkenes.
- To utilize fluoroform as the trifluoromethyl source.
- To synthesize β-trifluoromethyl alcohols from simple alkenes.
Main Methods:
- Generation of a [CuCF3] reagent from fluoroform.
- Reaction of the [CuCF3] reagent with alkenes in the presence of B2Pin2 and air.
- Characterization of the synthesized β-trifluoromethyl alcohols.
Main Results:
- Successful hydroxytrifluoromethylation of various alkenes was achieved.
- The reaction proceeds via addition of hydroxy and trifluoromethyl groups across the alkene double bond.
- The method provides a cost-effective route to β-trifluoromethyl alcohols using fluoroform.
Conclusions:
- A novel and efficient hydroxytrifluoromethylation of alkenes using fluoroform-derived [CuCF3] has been established.
- This method offers a sustainable and economical approach to synthesize valuable trifluoromethylated compounds.
- The developed protocol broadens the synthetic utility of fluoroform in organic synthesis.
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