Dual Role of Silanol Groups in Cyclopropanation and Hiyama-Denmark Cross-Coupling Reactions

作者:Beaulieu Louis Philippe B; Delvos Lukas B; Charette Andre B*
来源:Organic Letters, 2010, 12(6): 1348-1351.
DOI:10.1021/ol1002863

摘要

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.

  • 出版日期2010-3-19