4.8 Article

Photoredox Metal-Free Allylic Defluorinative Silylation of α-Trifluoromethylstyrenes with Hydrosilanes

Journal

ORGANIC LETTERS
Volume 24, Issue 23, Pages 4286-4291

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c01690

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Funding

  1. National Natural Science Foundation of China [22001217]
  2. Science and Technology Program of Sichuan Province [2021ZYD0064]

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We have developed an efficient strategy that combines organic photoredox and hydrogen atom transfer to prepare gem-difluoroallylsilanes via defluorinative silylation of alpha-trifluoromethylstyrenes using hydrosilanes as silicon sources. This environmentally friendly approach allows for the preparation of structurally diverse gem-difluoroallylsilanes with excellent functional group compatibility, making it suitable for late-stage modification of bioactive and complex molecules.
We report an efficient strategy that combines organic photoredox and hydrogen atom transfer to deliver gem-difluoroallylsilanes via defluorinative silylation of alpha-trifluoromethylstyrenes using hydrosilanes as silicon sources. This protocol provides an environmentally friendly approach for the preparation of structurally diverse gem-difluoroallylsilanes with excellent functional group compatibility and renders it suitable for late-stage modification of bioactive and complex molecules.

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