Activation of Trifluoromethylthio Moiety by Appending Iodonium Ylide under Copper Catalysis for Electrophilic Trifluoromethylation Reaction

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書誌事項

公開日
2016-03-08
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#am
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/cjoc.201600029
  • 10.1002/chin.201639043
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>A novel iodonium‐ylide compound <jats:bold>2 </jats:bold>that appends atrifluoromethylthio (SCF<jats:sub>3</jats:sub>) group is disclosed as a new, shelf‐stable electrophilic trifluoromethylation reagent. Unlike known shelf‐stable electrophilic trifluoromethylation reagents, <jats:bold>2</jats:bold> has a stable SCF<jats:sub>3</jats:sub> group which is activated by appending iodonium ylide under copper catalysis via sulfonium ylide to generate a cationic trifluoromethyl (CF<jats:sub>3</jats:sub>) species. Reagent <jats:bold>2</jats:bold> was found to be an efficient electrophilic trifluoromethylation reagent for a wide range of silyl enol ethers <jats:bold>3</jats:bold> under copper catalysis. Cyclic and acyclic <jats:italic>α</jats:italic>‐trifluoromethyl ketones <jats:bold>4</jats:bold> were obtained by reagent <jats:bold>2</jats:bold> in moderate to good yields. On the other hand, a difluoromethylthio analogue <jats:bold>5</jats:bold> did not affect intermolecular transfer difluoromethylation to substrates. Instead, intramolecular 1,4‐migration proceeded similar to the Stevens rearrangement to provide <jats:bold>6</jats:bold> in 21% yield, independent of the presence of nucleophiles <jats:bold>3</jats:bold>.</jats:p>

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