4.8 Article

Palladium-Catalyzed Dearomative Allylic Alkylation of Indoles with Alkynes To Synthesize Indolenines with C3-Quarternary Centers

Journal

ORGANIC LETTERS
Volume 18, Issue 15, Pages 3906-3909

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01947

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Funding

  1. National Natural Science Foundation of China [NSFC21572272, NSFC21502232]
  2. Natural Science Foundation of Jiangsu Province [BK20140655]
  3. Foundation of State Key Laboratory of Natural Medicines [ZZYQ201605]
  4. Innovative Research Team in University [IRT_15R63]

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A palladium-catalyzed dearomative allylic alkylation of indoles with alkynes to construct indolenines with C3-quarternary centers was reported. The in situ formed arylallene intermediate omitted the need to install leaving groups on the allylic compounds and employ extra oxidants to oxidize the allylic C-H bonds. The reaction exhibited good functional group tolerance and high atom economy. Moreover, the reaction was further expanded to synthesize pyrroloindolines and furanoindolines.

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