Siladifluoromethylation and Difluoromethylation onto C(sp3), C(sp2), and C(sp) Centers Using Ruppert–Prakash Reagent and Fluoroform

Siladifluoromethylation and Difluoromethylation onto C(sp3), C(sp2), and C(sp) Centers Using Ruppert–Prakash Reagent and Fluoroform

Siladifluoromethylations and difluoromethylations on sp3, sp2, and sp carbons of lithiated carbamates, arenes, and terminal alkynes, respectively, have been attained by employing the Ruppert–Prakash reagent (CF3TMS) and fluoroform (CF3H) as the CF2 sources. The advantage of this reaction is that the...

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Bibliographic Details
Published in:Organic letters Vol. 18; no. 14; pp. 3354 - 3357
Main Authors: Aikawa, Kohsuke, Maruyama, Kenichi, Nitta, Junki, Hashimoto, Ryota, Mikami, Koichi
Format: Journal Article
Language:English
Published: United States American Chemical Society 15-07-2016
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Summary:Siladifluoromethylations and difluoromethylations on sp3, sp2, and sp carbons of lithiated carbamates, arenes, and terminal alkynes, respectively, have been attained by employing the Ruppert–Prakash reagent (CF3TMS) and fluoroform (CF3H) as the CF2 sources. The advantage of this reaction is that the (sila)­difluoromethylated compounds can be obtained by simple treatment of easily accessible substrates, lithium bases, and CF3TMS or CF3H. Furthermore, the products bearing the TMS group can be transformed into the valuable compounds with the CF2 fragment via the carbon–carbon bond forming reactions.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01476