Synthesis of 2-substituted indoles and indolines via Suzuki-Miyaura coupling/5-endo-trig cyclization strategies

Haruhiko Fuwa, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

(Chemical Equation Presented) New strategies for the synthesis of 2-substituted indoles and indolines using acyclic, imide-derived enol phosphates, which were readily prepared from o-haloanilides, have been developed based on Suzuki-Miyaura coupling-cyclization sequences. A highly chemoselective cross-coupling of imide-derived enol phosphates with boron nucleophiles under Suzuki-Miyaura conditions allowed for the efficient preparation of various N-(o-halophenyl)enecarbamates that served as useful precursors for subsequent 5-endo-trig Heck or 5-endo-trig aryl radical cyclizations to furnish 2-substituted indoles or indolines, respectively. Furthermore, a one-pot Suzuki-Miyaura coupling-cyclization cascade starting from enol phosphates has been developed, which was successfully applied to the efficient synthesis of an indol-2-yl-1H-quinolin-2-one KDR inhibitor.

Original languageEnglish
Pages (from-to)212-221
Number of pages10
JournalJournal of Organic Chemistry
Volume74
Issue number1
DOIs
Publication statusPublished - 2009 Jan 2

ASJC Scopus subject areas

  • Organic Chemistry

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