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C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines
- Loach, Richard
P., Fenton, Owen S., Amaike, Kazuma, Siegel, Dustin S., Ozkal, Erhan, Movassaghi, Mohammad
- Journal of organic chemistry 2014 v.79 no.22 pp. 11254-11263
- catalytic activity, chemical reactions, chemical structure, organic chemistry, palladium, tryptamines, tryptophan
- 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.