C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines
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Movassaghi_C7-derivatization.pdf
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Author(s)
Loach, Richard Peter
Fenton, Owen S.
Amaike, Kazuma
Siegel, Dustin Scott
Ozkal, Erhan
Movassaghi, Mohammad
Date Issued
October 2014
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Loach, Richard P.; Fenton, Owen S.; Amaike, Kazuma; Siegel, Dustin S.; Ozkal, Erhan and Movassaghi, Mohammad. "C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines." 79, no. 22 (November 2014): 11254–11263 © 2014 American Chemical Society
Version
Final published version
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jo502062z
