Stereoselective synthesis of 3-alkylideneoxindoles by palladium-catalyzed cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents

Tomoya Miura, Takeharu Toyoshima, Yusuke Takahashi, Masahiro Murakami

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

(Chemical Equation Presented) A palladium(0)/monophosphine catalyst promotes a cyclization reaction of 2-(alkynyl)aryl isocyanates with organoboron reagents to produce stereodefined 3-alkylideneoxindoles. The alkynyl and isocyanato groups undergo oxidative cyclization with Pd(O) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

Original languageEnglish
Pages (from-to)4887-4889
Number of pages3
JournalOrganic Letters
Volume10
Issue number21
DOIs
Publication statusPublished - 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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