Visible Light-Promoted Aerobic Oxidation of α-Silyl Styrenes with Alcohols

Yan Tan; Bo Yang; Jiale Ying; Bing Yu; Zhan Lu

doi:10.1002/cjoc.202400602

Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3243 -3247. DOI: 10.1002/cjoc.202400602

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Visible Light-Promoted Aerobic Oxidation of α-Silyl Styrenes with Alcohols

Yan Tan ¹
, Bo Yang ²
, Jiale Ying ²
, Bing Yu ¹
, Zhan Lu ¹^,²^,^†

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Abstract

Comprehensive Summary:A mechanistically distinctive visible-light-promoted metal-free aerobic oxidation of alkenyl silanes with alcohols was disclosed to efficiently construct α-alkoxy ketones under mild conditions. The primary, secondary, and tertiary alcohols could be used as reactants. The protocol could be carried out on a gram-scale. Various derivatizations of products could be conducted. Mechanistic studies indicated the reaction was initiated by single-electron oxidation of the alkenyl silanes, rather than radical addition to alkenyl silanes.

Keywords

Alkenyl silanes / Aerobic oxidation / Alcohols / α-Alkoxy ketones / Visible light photocatalysis / Radical reactions / Synthetic methods / Redox reactions

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Yan Tan, Bo Yang, Jiale Ying, Bing Yu, Zhan Lu. Visible Light-Promoted Aerobic Oxidation of α-Silyl Styrenes with Alcohols. Chinese Journal of Chemistry, 2024, 42(24): 3243-3247 DOI:10.1002/cjoc.202400602