Issue 11, 2019

Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes

Abstract

The reaction of N-heteroaromatic compounds, such as 2-aryl-pyrrole, benzimidazole, imidazole, indole, and pyrazole derivatives, with alkynes in the presence of a catalytic amount of a nickel complex results in C–H/N–H oxidative annulation. The reaction shows a high functional group compatibility. While both Ni(0) and Ni(II) complexes show a high catalytic activity, Ni(0) is proposed as a key catalytic species in the main catalytic cycle. In the case of the Ni(II) system, the presence of a catalytic amount of a strong base, such as KOBut, is required for the reaction to proceed. In sharp contrast, a base is not required in the case of the Ni(0) system. The proposed mechanism is supported by DFT studies.

Graphical abstract: Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes

Supplementary files

Article information

Article type
Edge Article
Submitted
14 11月 2018
Accepted
03 2月 2019
First published
04 2月 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3242-3248

Nickel-catalyzed oxidative C–H/N–H annulation of N-heteroaromatic compounds with alkynes

A. Obata, A. Sasagawa, K. Yamazaki, Y. Ano and N. Chatani, Chem. Sci., 2019, 10, 3242 DOI: 10.1039/C8SC05063E

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