Ni(0)-Catalyzed Regiocontrolled Sila-Alkenylation of Aldehydes: A Heteroatom Inclusive Strategy

We report a Ni<sup>0</sup>-catalyzed regiocontrolled sila-alkenylation of <i>O</i>-allyl salicylaldehydes, enabling the synthesis of a diverse array of chromanols with exclusive <i>syn</i> selectivity. The methodology can also be applied to the construction of N-heterocycles and carbocycles. The Et<sub>3</sub>B/Et<sub>3</sub>SiH combination circumvents the key challenges to provide selective β-hydride elimination. The reaction order dependence was determined for each component of the reaction.

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Publication Details

Journal
Organic Letters
Published
2025-11-05
DOI
https://doi.org/10.1021/acs.orglett.5c03947
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94
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article

Ni(0)-Catalyzed Regiocontrolled Sila-Alkenylation of Aldehydes: A Heteroatom Inclusive Strategy

Aankhi Khamrai, Sudipta Ghosh, Venkataraman Ganesh
1 citations
Organic Letters
Catalytic C–H Functionalization Methods
0.94
article

Ni(0)-Catalyzed Regiocontrolled Sila-Alkenylation of Aldehydes: A Heteroatom Inclusive Strategy

Aankhi Khamrai, Sudipta Ghosh, Venkataraman Ganesh
article en
1 citations

Abstract

We report a Ni<sup>0</sup>-catalyzed regiocontrolled sila-alkenylation of <i>O</i>-allyl salicylaldehydes, enabling the synthesis of a diverse array of chromanols with exclusive <i>syn</i> selectivity. The methodology can also be applied to the construction of N-heterocycles and carbocycles. The Et<sub>3</sub>B/Et<sub>3</sub>SiH combination circumvents the key challenges to provide selective β-hydride elimination. The reaction order dependence was determined for each component of the reaction.

Organic LettersVol. 27(45)
Indian Institute of Technology Kharagpur (IN)
Openalex Percentile: Top 20%
Catalytic C–H Functionalization Methods
0.94
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