Issue 2, 2025

Direct arylation of gem-difluorostyrenes using in situ mechanochemically generated calcium-based heavy Grignard reagents

Abstract

In this study, we disclosed that calcium-based heavy Grignard reagents, prepared in situ through a mechanochemical method, reacted with gem-difluorostyrenes in the absence of transition-metal catalysts to afford thermodynamically less favorable (E)-monofluorostilbenes with good to high stereoselectivity. To the best of our knowledge, this is the first example of nucleophilic substitution of a C(sp2)–F bond by an arylcalcium compound.

Graphical abstract: Direct arylation of gem-difluorostyrenes using in situ mechanochemically generated calcium-based heavy Grignard reagents

Supplementary files

Article information

Article type
Paper
Submitted
19 Nov 2024
Accepted
21 Dec 2024
First published
25 Dec 2024
This article is Open Access
Creative Commons BY-NC license

RSC Mechanochem., 2025,2, 256-262

Direct arylation of gem-difluorostyrenes using in situ mechanochemically generated calcium-based heavy Grignard reagents

X. Wang, Y. Fukuzawa, P. Gao, J. Jiang, S. Maeda, K. Kubota and H. Ito, RSC Mechanochem., 2025, 2, 256 DOI: 10.1039/D4MR00135D

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