Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer

Carboxylic acids are bench-stable and readily available chemical feedstocks that function as optimal and fundamental synthetic platforms for the construction of C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bonds via decarboxylation processes. We present a novel and practical protocol for the decarboxylative alkylation of Morita-Baylis-Hillman acetates with various carboxylic acids via a photoinduced iron-mediated ligand-to-metal charge transfer (LMCT) process under redox-neutral conditions. This method exhibits remarkable tolerance to a wide array of carboxylic acids, including primary, secondary, and tertiary carboxylic acids, obviating the requirement for preactivated radical precursors. The preliminary mechanistic analyses indicate that a radical pathway is involved in this catalytic transformation.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-02-28
DOI
https://doi.org/10.1021/acs.joc.4c03047
Citations
11
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
10.30

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article

Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer

Yuxuan Zheng, Mingsong Shi, De-Jun Cheng, Qiwang Hou et al.
11 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
10.30
article

Decarboxylative Alkylation of Morita–Baylis–Hillman Acetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-Metal Charge Transfer

Yuxuan Zheng, Mingsong Shi, De-Jun Cheng, Qiwang Hou, Lin‐Hai Jing, Hui Zhang, Ziyi Guo, Yu-Tong Mei, Dan Yang
article en
11 citations

Abstract

Carboxylic acids are bench-stable and readily available chemical feedstocks that function as optimal and fundamental synthetic platforms for the construction of C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bonds via decarboxylation processes. We present a novel and practical protocol for the decarboxylative alkylation of Morita-Baylis-Hillman acetates with various carboxylic acids via a photoinduced iron-mediated ligand-to-metal charge transfer (LMCT) process under redox-neutral conditions. This method exhibits remarkable tolerance to a wide array of carboxylic acids, including primary, secondary, and tertiary carboxylic acids, obviating the requirement for preactivated radical precursors. The preliminary mechanistic analyses indicate that a radical pathway is involved in this catalytic transformation.

The Journal of Organic ChemistryVol. 90(10)
University of Electronic Science and Technology of China (CN), China West Normal University (CN), Mianyang Central Hospital (CN), Chemical Synthesis Lab (SG), Sichuan University of Science and Engineering (CN)
National Natural Science Foundation of China, Fundamental Research Funds of China West Normal University
Openalex Percentile: Top 2%
Catalytic C–H Functionalization Methods
10.30
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