Silylative coupling of olefins with vinylsilanes in the synthesis of functionalized alkenes
Authors:
- Justyna Szudkowska-Frątczak,
- Grzegorz Hreczycho,
- Piotr Pawluć
Abstract
The development of highly selective methods for the synthesis of functionalized olefins, based on sequential catalytic reactions of organometallic reagents, has been the subject of extensive study because of their versatile applications in organic synthesis and materials science. The silylative coupling of olefins with vinyl-substituted organosilicon compounds (discovered in our group) represents one of the most efficient and straightforward methods for the synthesis of stereodefined alkenylsilanes and bis(silyl)alkenes, which are particularly attractive scaffolds for further transformations including palladium-catalyzed cross-coupling with organic halides (Hiyama coupling) or electrophile-induced desilylation. The article highlights the recent developments and covers the literature mainly from the last decade in the sequential (also one-pot) synthetic strategies including ruthenium-catalyzed silylative coupling followed by desilylative cross-coupling, acylation and halogenation, leading to stereodefined organic derivatives such as (E)-alkenyl halides, (E)-α,β-unsaturated ketones or arylene-(E)-vinylene derivatives which are widely applied as fine chemicals, functional materials or building blocks in organic synthesis.
- Record ID
- UAM8d0654586ad84611be2d1208d94ead52
- Author
- Journal series
- Organic Chemistry Frontiers, ISSN 2052-4129
- Issue year
- 2015
- Vol
- 2
- Pages
- 730-738
- ASJC Classification
- DOI
- DOI:10.1039/c5qo00018a Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 40
- Score source
- journalList
- Score
- Publication indicators
- = 17; = 25; : 2015 = 0.888; : 2015 (2 years) = 4.693 - 2015 (5 years) =4.699
- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM8d0654586ad84611be2d1208d94ead52/
- URN
urn:amu-prod:UAM8d0654586ad84611be2d1208d94ead52
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.