Nickel-catalyzed synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes

Fluorine-bearing silanes have displayed widespread applications in organic synthesis and inorganic and material chemistry due to their high reactivity and versatility.However, the synthesis of fluorine-containing compounds featuring a difluorine-bearing silane is still underdeveloped.Here, we reported a simple, mild and efficient method for halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes with bromodifluoroacetates under nickel catalysis, affording a variety of fluorine-bearing silanes in up to 89 % yield.This research was distinguished by its good functional group tolerance, moderate to good yields and exclusive regioselectivity.

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Publication Details

Journal
Tetrahedron Chem
Published
2025-04-14
DOI
https://doi.org/10.1016/j.tchem.2025.100129
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Nickel-catalyzed synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes

Wenxin Lu, Ting Su, Qinglei Chong, Fanke Meng et al.
Tetrahedron Chem
Fluorine in Organic Chemistry
article

Nickel-catalyzed synthesis of fluorine-bearing silane through halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes

Wenxin Lu, Ting Su, Qinglei Chong, Fanke Meng, Wei Huang, Heng Wang
article en

Abstract

Fluorine-bearing silanes have displayed widespread applications in organic synthesis and inorganic and material chemistry due to their high reactivity and versatility.However, the synthesis of fluorine-containing compounds featuring a difluorine-bearing silane is still underdeveloped.Here, we reported a simple, mild and efficient method for halofluoroalkylation and hydrofluoroalkylation of alkenylsilanes with bromodifluoroacetates under nickel catalysis, affording a variety of fluorine-bearing silanes in up to 89 % yield.This research was distinguished by its good functional group tolerance, moderate to good yields and exclusive regioselectivity.

Tetrahedron ChemVol. 14
University of California, Santa Barbara (US), Yale University (US), Shanghai Institute of Organic Chemistry (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, Science and Technology Commission of Shanghai Municipality, Nankai University, Beijing National Laboratory for Molecular Sciences
Openalex Percentile: Top 94%
Fluorine in Organic Chemistry
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