Strategic Applications of the β-Silicon Effect

Roberts, Dean and McLaughlin, Mark (2022) Strategic Applications of the β-Silicon Effect. Advanced Synthesis & Catalysis, 364 (14). pp. 2307-2332. ISSN 1615-4150

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Abstract

Organosilicon reagents are highly versatile and privileged scaffolds in modern synthetic chemistry, largely due to the range of transformations the groups are amenable to. The β-Silicon effect is one of the fundamental phenomena underpinning the inherent reactivity of organosilicon reagents, allowing unsaturated organosilanes to undergo a range of electrophilic substitutions with a variety of nucleophiles. The application of the β-Silicon effect in a range of organic transformations is reviewed with the discussion divided up based on the class of silane. The reactivity of these compounds towards carbon, heteroatom and metallic electrophiles is discussed from classical applications such as the Sakurai allylation to contemporary applications such as cross-coupling chemistry. In addition, examples of these transformations in the context of methodology development and natural product synthesis are provided.

Item Type:
Journal Article
Journal or Publication Title:
Advanced Synthesis & Catalysis
Additional Information:
This is the peer reviewed version of the following article:Roberts, D.D. and McLaughlin, M.G. (2022), Strategic Applications of the β-Silicon Effect. Adv. Synth. Catal.. https://doi.org/10.1002/adsc.202200237 which has been published in final form at https://onlinelibrary.wiley.com/doi/10.1002/adsc.202200237 This article may be used for non-commercial purposes in accordance With Wiley Terms and Conditions for self-archiving.
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ID Code:
171936
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Deposited On:
16 Jun 2022 13:40
Refereed?:
Yes
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Published
Last Modified:
22 Nov 2022 11:29