4.7 Article

Synthesis of 2-(Arylthio)indolenines via Chemoselective Arylation of Thio-Oxindoles with Arynes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 13, Pages 2683-2688

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202000308

Keywords

Chemoselective S-arylation; thio-oxindoles; Aryne; 2-(Arylthio)indolenines; Chemical space

Funding

  1. National Natural Science Foundation of China [21702013]
  2. Fundamental Research Funds for the Central Universities [XK1802-6, buctrc201721]
  3. Shaanxi University of Science and Technology [BJ15-33]

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A chemoselective S-arylation reaction of thio-oxindoles with arynes is presented. The reaction was performed under mild conditions and provided a straightforward synthesis of 2-(arylthio)indolenines in good to excellent yields. Besides, this simple operational protocol is not only scalable but also has good functional group compatibilities and substrate scope. Thus, our protocol should allow for the expansion of chemical space via developing new scaffolds of thioimidates that are difficult to synthesize otherwise.

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