Journal of the American Chemical Society p. 13136 - 13144 (2020)
Update date:2022-08-11
Topics:
Tian, Ya-Ming
Guo, Xiao-Ning
Wu, Zhu
Friedrich, Alexandra
Westcott, Stephen A.
Braunschweig, Holger
Radius, Udo
Marder, Todd B.
A highly efficient and general protocol for traceless, directed C3-selective C-H borylation of indoles with [Ni(IMes)2] as the catalyst is reported. Activation and borylation of N-H bonds by [Ni(IMes)2] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C-H bonds. The N-Bpin group which is formed is easily converted in situ back to an N-H group by the oxidative addition product of [Ni(IMes)2] and in situ-generated HBpin. The catalytic reactions are operationally simple, allowing borylation of a variety of substituted indoles with B2pin2 in excellent yields and with high selectivity. The C-H borylation can be followed by Suzuki-Miyaura cross-coupling of the C-borylated indoles in an overall two-step, one-pot process providing an efficient method for synthesizing C3-functionalized heteroarenes.
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