Nickel-Catalyzed C–F/N–H Annulation of 2-(2-Fluoroaryl) N-Heteroaromatic Compounds with Alkynes: Activation of C–F Bonds

Dedicated to Professor Shinji Murai for his contribution to bond activation

Abstract

The reaction of 2-(2-fluoroaryl) N-heteroaromatic compounds, such as benzimidazole and indole derivatives, with internal alkynes in the presence of a catalytic amount of a nickel complex results in C–F/N–H annulation with alkynes. The reaction shows a high functional group compatibility. The presence of a strong base, such as KOBu­ ^t or LiOBu ^t , is required for the reaction to proceed.

Key words

C–F bond activation - nickel - alkyne - annulation - N-heteroaromatic compounds

Publication History

Received: 01 December 2020

Accepted after revision: 15 December 2020

Accepted Manuscript online:
15 December 2020

Article published online:
21 January 2021

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