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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Final published version
Research output: Contribution to Journal/Magazine › Review article › peer-review
Research output: Contribution to Journal/Magazine › Review article › peer-review
}
TY - JOUR
T1 - Strategic Applications of the β-Silicon Effect
AU - Roberts, Dean
AU - McLaughlin, Mark
N1 - 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.
PY - 2022/7/19
Y1 - 2022/7/19
N2 - 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.
AB - 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.
KW - allylation, carbocations
KW - catalysis
KW - organosilicon
KW - Sakurai allylation
KW - silicon
KW - target synthesis
U2 - 10.1002/adsc.202200237
DO - 10.1002/adsc.202200237
M3 - Review article
VL - 364
SP - 2307
EP - 2332
JO - Advanced Synthesis & Catalysis
JF - Advanced Synthesis & Catalysis
SN - 1615-4150
IS - 14
ER -