4.8 Article

Stereoselective Synthesis of 3-Alkylideneoxindoles by Palladium-Catalyzed Cyclization Reaction of 2-(Alkynyl)aryl Isocyanates with Organoboron Reagents

Journal

ORGANIC LETTERS
Volume 10, Issue 21, Pages 4887-4889

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801844w

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Funding

  1. Mizuho Foundation for the Promotion of Sciences and the Ministry of Education, Culture, Sports, Science and Technology of Japan [18032040, 20750078]
  2. Grants-in-Aid for Scientific Research [20750078, 18032040] Funding Source: KAKEN

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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(0) to form an oxapalladacycle intermediate. Subsequent transmetalation and reductive elimination afford the product.

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