DecarboxylativeAlkylation of Morita–Baylis–HillmanAcetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-MetalCharge 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.

Publication Details

Journal
Figshare
Published
2025-02-28
DOI
https://doi.org/10.1021/acs.joc.4c03047.s001
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Libraries and Information Services
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article
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article

DecarboxylativeAlkylation of Morita–Baylis–HillmanAcetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-MetalCharge Transfer

Figshare
Libraries and Information Services
article

DecarboxylativeAlkylation of Morita–Baylis–HillmanAcetates with Aliphatic Acids via Photochemical Iron-Mediated Ligand-to-MetalCharge Transfer

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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.

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Libraries and Information Services
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