Nickel-catalyzed stereo-controlled 2,3-hydrosilylation of 1,1-disubstituted allenes

Directing regioselectivity and stereoselectivity in allene reactions has long been a significant challenge due to the multiple reactive pathways available. In this study, we report the development of a Ni-catalyzed regio- and stereoselective 2,3-hydrosilylation of 1,1-disubstituted allenes. Stereoselectivity was precisely controlled through the strategic modulation of ligand-induced steric effects and non-covalent interactions. Phenyl dibenzophosphole as the ligand enabled the selective formation of (<i>Z</i>)-allylsilanes, while tricyclohexylphosphine favored the production of (<i>E</i>)-allylsilanes. This work highlights the critical role of ligand-induced steric and non-covalent interactions in dictating regio- and stereoselectivity, offering new insights into Ni(ii) catalysis for stereoselective hydrosilylation.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc01148e
Citations
5
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
2.69

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article

Nickel-catalyzed stereo-controlled 2,3-hydrosilylation of 1,1-disubstituted allenes

Eun Jin Cho, Shrikant D. Tambe, Ji‐Hoon Jang, Seoyeon Kim et al.
5 citations
Chemical Science
Asymmetric Hydrogenation and Catalysis
2.69
article

Nickel-catalyzed stereo-controlled 2,3-hydrosilylation of 1,1-disubstituted allenes

Eun Jin Cho, Shrikant D. Tambe, Ji‐Hoon Jang, Seoyeon Kim, Jin A Kim
article en
5 citations

Abstract

Directing regioselectivity and stereoselectivity in allene reactions has long been a significant challenge due to the multiple reactive pathways available. In this study, we report the development of a Ni-catalyzed regio- and stereoselective 2,3-hydrosilylation of 1,1-disubstituted allenes. Stereoselectivity was precisely controlled through the strategic modulation of ligand-induced steric effects and non-covalent interactions. Phenyl dibenzophosphole as the ligand enabled the selective formation of (<i>Z</i>)-allylsilanes, while tricyclohexylphosphine favored the production of (<i>E</i>)-allylsilanes. This work highlights the critical role of ligand-induced steric and non-covalent interactions in dictating regio- and stereoselectivity, offering new insights into Ni(ii) catalysis for stereoselective hydrosilylation.

Chemical ScienceVol. 16(17)
Chung-Ang University (KR)
National Research Foundation, National Research Foundation of Korea
Openalex Percentile: Top 10%
Asymmetric Hydrogenation and Catalysis
2.69
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