Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 22, Pages 11254-11263Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo502062z
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Funding
- NIH-NIGMS [GM089732, GM074825]
- NSF under CCI Center for selective C-H functionalization [CHE-1205646]
- Fonds de Recherche du Quebec-Nature et Technologies
- Institute of Transformative Bio-Molecules, Nagoya University
- NSF program for Science Across Virtual Institutes
- MECYD
- Grants-in-Aid for Scientific Research [13J03924] Funding Source: KAKEN
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1205646] Funding Source: National Science Foundation
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A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronationC2-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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