Journal
ORGANIC LETTERS
Volume 12, Issue 6, Pages 1348-1351Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1002863
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- NSERC (Canada)
- Canada Research Chair Program
- Canada Foundation for Innovation
- Universite de Montreal
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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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