Visible-Light Induced Dehydrogenative Cross-Coupling of Enamides with Hydrocarbons Enabled by Aryl Thianthrenium Salt

Herein, we present a photocatalytic β-C(sp<sup>2</sup>)-H alkylation of enamides with easily accessible hydrocarbons under mild conditions. The utilization of aryl thianthrenium salt as a hydrogen-atom transfer (HAT) precursor enables the smooth generation of diverse carbon-centered radicals from chemical feedstocks containing hydridic or protic C-H bonds. Noteworthy features of this protocol encompass high step efficiency, good functional group compatibility, and excellent chemo-, regio-, and stereoselectivity. Mechanistic experiments and density functional theory (DFT) calculations support the involvement of an electron donor-acceptor (EDA) complex.

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Publication Details

Journal
Organic Letters
Published
2026-03-26
DOI
https://doi.org/10.1021/acs.orglett.6c00763
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible-Light Induced Dehydrogenative Cross-Coupling of Enamides with Hydrocarbons Enabled by Aryl Thianthrenium Salt

Xiao-ya LU, Yue Wang, Yali Li, Jian Han et al.
Organic Letters
Radical Photochemical Reactions
article

Visible-Light Induced Dehydrogenative Cross-Coupling of Enamides with Hydrocarbons Enabled by Aryl Thianthrenium Salt

Xiao-ya LU, Yue Wang, Yali Li, Jian Han, Li-Li Zeng, Fen-Er Chen, Qiu-Ru Zhang
article en

Abstract

Herein, we present a photocatalytic β-C(sp<sup>2</sup>)-H alkylation of enamides with easily accessible hydrocarbons under mild conditions. The utilization of aryl thianthrenium salt as a hydrogen-atom transfer (HAT) precursor enables the smooth generation of diverse carbon-centered radicals from chemical feedstocks containing hydridic or protic C-H bonds. Noteworthy features of this protocol encompass high step efficiency, good functional group compatibility, and excellent chemo-, regio-, and stereoselectivity. Mechanistic experiments and density functional theory (DFT) calculations support the involvement of an electron donor-acceptor (EDA) complex.

Organic Letters
Fudan University (CN), Shijiazhuang Yiling Pharmaceutical (China) (CN), Changzhou University (CN), Chemical Synthesis Lab (SG)
Openalex Percentile: Top 7%
Radical Photochemical Reactions
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