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C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines

Authors
  • Loach, Richard P.
  • Fenton, Owen S.
  • Amaike, Kazuma
  • Siegel, Dustin S.
  • Ozkal, Erhan
  • Mo Movassaghi
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Jan 14, 2014
Volume
79
Issue
22
Pages
79–11254
Identifiers
DOI: 10.1021/jo502062z
Source
CCHF
License
White

Abstract

A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation–C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-boroindoles that enable further C7-derivatization. The versatility of the chemistry is highlighted by the gram-scale synthesis of C7-boronated N-Boc-L-tryptophan methyl ester and the rapid synthesis of C7-halo, C7-hydroxy, and C7-aryl tryptophan derivatives.

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