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    Rights statement: 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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    Embargo ends: 2/06/23

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Strategic Applications of the β-Silicon Effect

Research output: Contribution to Journal/MagazineReview articlepeer-review

Published
<mark>Journal publication date</mark>19/07/2022
<mark>Journal</mark>Advanced Synthesis & Catalysis
Issue number14
Volume364
Number of pages27
Pages (from-to)2307-2332
Publication StatusPublished
Early online date2/06/22
<mark>Original language</mark>English

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.

Bibliographic note

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.