4.8 Article

Palladium-Catalyzed Insertion of Isocyanides into the C-S Bonds of Heteroaryl Sulfides

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 22, Pages 6653-6657

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802369

Keywords

heterocycles; isocyanides; palladium thioesters; synthetic methods

Funding

  1. JSPS KAKENHI [JP16H01019, JP16H011439, JP16H04109, JP16H06887, JP18H04254, JP18H04409, JP18K14212]
  2. JST ACT-C, Japan [JPMJCR12ZE]
  3. JSPS Predoctoral Fellowship

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Insertion of tort-butyl isocyanide into the C(sp(2))-S bonds of heteroaryl sulfides is catalyzed by a palladium diphosphine complex. Thioimidates generated through this reaction could be readily hydrolyzed under acidic conditions to yield the corresponding thioesters, which are of synthetic use. Phis insertion is useful because starting heteroaryl sulfides were readily prepared by either conventional ways or through sulfur-specific extended Punimerer reactions.

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