Synthesis of 3-iminoindol-2-amines and cyclic enaminones via palladium-catalyzed isocyanide insertion-cyclization

Yuan Yuan Pan, Ya Nan Wu, Zhen Zhen Chen, Wen Juan Hao, Guigen Li, Shu Jiang Tu, Bo Jiang

Research output: Contribution to journalArticle

50 Scopus citations

Abstract

A palladium-catalyzed isocyanide insertion-cyclization using low-cost and readily accessible 2-haloanilines, 2-iodophenylethanones, and isocyanides for efficient synthesis of 3-iminoindol-2-amine and cyclic enaminone derivatives has been developed. The method features low-cost and readily accessible starting materials, reliable scalability, and bond-forming efficiency as well as simple one-pot operation, which makes this strategy highly attractive. A reasonable mechanism for forming 3-iminoindol-2-amine involved double isocyanide insertion/cyclization process is proposed.

Original languageEnglish
Pages (from-to)5764-5770
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number11
DOIs
StatePublished - Jun 5 2015

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