Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis

Difluoromethanesulfonyl hypervalent iodonium ylides 2 were developed as electrophilic difluoromethylthiolation reagents for a wide range of nucleophiles. Enamines, indoles, β-keto esters, silyl enol ethers and pyrroles were effectively reacted with 2 affording desired difluoromethylthio (SCF2H)-subs...

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Published inRoyal Society open science Vol. 3; no. 5; p. 160102
Main Authors Arimori, Sadayuki, Matsubara, Okiya, Takada, Masahiro, Shiro, Motoo, Shibata, Norio
Format Journal Article
LanguageEnglish
Published England The Royal Society 01.05.2016
Subjects
Carbene
Chemistry
Difluoromethylthiolation
Fluorine
Hypervalent Iodonium Ylide
Sulfur
difluoromethylthiolation
sulfur
hypervalent iodonium ylide
carbene
fluorine
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ISSN2054-5703
2054-5703
DOI10.1098/rsos.160102

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Summary:Difluoromethanesulfonyl hypervalent iodonium ylides 2 were developed as electrophilic difluoromethylthiolation reagents for a wide range of nucleophiles. Enamines, indoles, β-keto esters, silyl enol ethers and pyrroles were effectively reacted with 2 affording desired difluoromethylthio (SCF2H)-substituted compounds in good to high yields under copper catalysis. The reaction of allyl alcohols with 2 under the same conditions provided difluoromethylsulfinyl (S(O)CF2H) products in good yields. The difluoromethylthiolation of enamines is particularly effective with wide generality, thus the enamine method was nicely extended to the synthesis of a series of difluoromethythiolated cyclic and acyclic β-keto esters, 1,3-diketones, pyrazole and pyrimidine derivatives by a consecutive, two-step one-pot reaction using 2.
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This article has been edited by the Royal Society of Chemistry, including the commissioning, peer review process and editorial aspects up to the point of acceptance.
ISSN:2054-5703
2054-5703
DOI:10.1098/rsos.160102