Direct C4-Benzylation of Indoles via Tandem Benzyl Claisen/Cope Rearrangements

Takumi Abe, Yuta Kosaka, Miku Asano, Natsuki Harasawa, Akane Mishina, Misato Nagasue, Yuri Sugimoto, Kazuaki Katakawa, Shunsuke Sueki, Masahiro Anada, Koji Yamada

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)


A novel direct C4 benzylation of indoles utilizing 2-benzyloxyindoles has been developed to access 4-benzyl-2-oxindoles. This strategy involves the in situ formation of isotoluene intermediates via benzyl Claisen rearrangements, which undergoes Cope rearrangement and aromatization. The method provides the desired products in moderate to high yields and shows good functional group tolerance.

Original languageEnglish
Pages (from-to)826-829
Number of pages4
JournalOrganic Letters
Issue number3
Publication statusPublished - Feb 1 2019
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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