EFFICIENT SYNTHESIS OF 3-BORYLATED INDOLINES VIA COBALT-CATALYZED DEAROMATIVE BORYLATION OF INDOLES

Authors

  • Oleksandr V. Vashchenko Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01033 https://orcid.org/0000-0002-5666-5592
  • Tetyana V. Bondarchuk Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01033
  • Ilona V. Raspertova Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01033 https://orcid.org/0000-0002-2382-063X
  • Valerii O. Bukhanko Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01033
  • Dmytro M. Khomenko Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01033. Enamine Ltd., 78 Winston Churchill St., Kyiv 02094 https://orcid.org/0000-0001-7058-832X
  • Rostyslav D. Lampeka Taras Shevchenko National University of Kyiv, 64/13 Volodymyrska St., Kyiv 01033 https://orcid.org/0000-0001-8326-4535

Keywords:

borylation, dearomatization, indole, indoline, cobalt(II), terpyridine, trifluoroborates

Abstract

The high efficiency of the cobalt(II) terpyridine complex as a precatalyst in the dearomative borylation of indoles using pinacolborane as the borylation agent was demonstrated. The reaction was tested on a series of indoles bearing substituents of different nature at the C-5 position of the indole ring and with various electron-withdrawing protecting groups on the indole nitrogen. The applicability of the proposed synthetic protocol for gram-scale synthesis was also demonstrated. The resulting pinacolboranes were subsequently converted into the corresponding boron fluorides with high yields.

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Published

2026-02-24

Issue

Vol. 61 No. 9/10 (2025): Modern catalytic approaches for the assembly and functionalization of heterocyclic compounds

Section

Original Papers