Dual role of silanol groups in cyclopropanation and Hiyama-Denmark cross-coupling reactions
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Updated: Jun 15, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Louis-Philippe B Beaulieu1, Lukas B Delvos, André B Charette
1Département de Chimie, Université de Montreal, P.O. Box. 6138, Station Downtown Montréal, Québec, Canada H3C 3J7.
Abstract:
Di-tert-butoxy(alkenyl)silanols serve as substrates in the Simmons-Smith cyclopropanation reaction furnishing the corresponding di-tert-butoxy(cyclopropyl)silanols, which may be included in a Hiyama-Denmark cross-coupling reaction. The silanol group bears two distinct roles as it provides a directing group during the cyclopropanation and mediates the transmetalation event in the cross-coupling. The nature of the ligands on the silicon atom had a profound effect on reactivity in the cross-coupling, whereby substituting the alkoxide groups for fluorides allowed for efficient cross-coupling.
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