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Arimori S, Matsubara O, Takada M, et al. Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. R Soc Open Sci. 2016;3(5):160102doi: 10.1098/rsos.160102.
Arimori, S., Matsubara, O., Takada, M., Shiro, M., & Shibata, N. (2016). Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. Royal Society open science, 3(5), 160102. https://doi.org/10.1098/rsos.160102
Arimori, Sadayuki, et al. "Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis." Royal Society open science vol. 3,5 (2016): 160102. doi: https://doi.org/10.1098/rsos.160102
Arimori S, Matsubara O, Takada M, Shiro M, Shibata N. Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis. R Soc Open Sci. 2016 May 25;3(5):160102. doi: 10.1098/rsos.160102. eCollection 2016 May. PMID: 27293790; PMCID: PMC4892452.
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R Soc Open Sci. 2016 May 25;3(5):160102. doi: 10.1098/rsos.160102. eCollection 2016 May.

Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis.

Royal Society open science

Sadayuki Arimori, Okiya Matsubara, Masahiro Takada, Motoo Shiro, Norio Shibata

Affiliations

  1. Department of Frontier Materials , Nagoya Institute of Technology , Gokiso, Showa-ku, Nagoya 466-8555 , Japan.
  2. Rigaku Corporation , 3-9-12 Matsubara-cho, Akishima, Tokyo 196-8666 , Japan.

PMID: 27293790 PMCID: PMC4892452 DOI: 10.1098/rsos.160102

Abstract

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.

Keywords: carbene; difluoromethylthiolation; fluorine; hypervalent iodonium ylide; sulfur

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