Ni-Catalyzed Traceless, Directed C3-Selective C-H Borylation of Indoles

Ya-Ming Tian, Xiao-Ning Guo*, Zhu Wu, Alexandra Friedrich, Stephen A. Westcott, Holger Braunschweig, Udo Radius* and Todd B. Marder*

*Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany, Email: guo.xiaoninguni-wuerzburg.de, u.radiusuni-wuerzburg.de, todd.marderuni-wuerzburg.de

Y.-M. Tian, X.-N. Guo, Z. Wu, A. Friedrich, S. A. Westcott, H. Braunschweig, U. Radius, T. B. Marder, J. Am. Chem. Soc., 2020, 142, 13136-13144.

DOI: 10.1021/jacs.0c05434

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Abstract

In a highly efficient and general protocol for a regioselective C-H borylation of indoles with [Ni(IMes)₂] as the catalyst, the reversible borylation of the nitrogen as a traceless directing group enables the C3-selective borylation of C-H bonds. A subsequent Suzuki-Miyaura cross-coupling of the C-borylated indoles in a one-pot process provides C3-functionalized heteroarenes.

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Key Words

indoles, borylation

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ID: J48-Y2020