Transition Metal‐Free Trifluoromethylation of <i>N</i>‐Allylamides with Sodium Trifluoromethanesulfinate: Synthesis of Trifluoromethyl‐Containing Oxazolines

書誌事項

公開日
2014-11-05
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/adsc.201400144
公開者
Wiley

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説明

<jats:title>Abstract</jats:title><jats:p>A transition metal‐free method for the trifluoromethylation of <jats:italic>N</jats:italic>‐allylamides has been developed, and the corresponding trifluoromethyl‐containing oxazolines were prepared in moderate to good yields. The protocol uses readily available substituted <jats:italic>N</jats:italic>‐allylamides as the starting materials, inexpensive and easily stored sodium trifluoromethanesulfinate as the trifluoromethyl source, iodobenzene diacetate as the oxidant, and the procedure involves sequential intermolecular trifluoromethylation of alkenes with sodium trifluoromethanesulfinate and intramolecular cyclization. This is the first example to prepare CF<jats:sub>3</jats:sub>‐containing oxazolines. Therefore, the present method should afford an efficient and practical strategy for synthesis of other CF<jats:sub>3</jats:sub>‐containing cyclic compounds.</jats:p><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/gif" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/mcontent.gif"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text></jats:p>

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