Dehydrogenative Cycloisomerization/Arylation Sequence of N-Propargyl Carboxamides with Arenes by Iodine(III)-Catalysis

Yuki Umakoshi, Yusuke Takemoto, Akira Tsubouchi, Viktor V. Zhdankin, Akira Yoshimura, Akio Saito

Research output: Contribution to journalArticlepeer-review

Abstract

Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile-tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)-catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from N-propargyl carboxamides and arenes, representing first C(sp3)−C(sp2) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in exo-dig modes. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)2053-2059
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number12
DOIs
StatePublished - Jun 21 2022

Bibliographical note

Funding Information:
This work was supported partly by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JPMJCR19R2). V.V.Z. and A.Y. are thankful to National Science Foundation (CHE‐1759798).

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

  • arylation
  • catalysis
  • cyclization
  • iodine
  • metal-free

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