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.
Authors
- Yuxuan Zheng (ORCID: https://orcid.org/0000-0002-6127-5169)
- Mingsong Shi (ORCID: https://orcid.org/0000-0002-8979-5844)
- De-Jun Cheng (ORCID: https://orcid.org/0009-0005-0258-012X)
- Qiwang Hou
- Lin‐Hai Jing (ORCID: https://orcid.org/0000-0001-6424-4491)
- Hui Zhang (ORCID: https://orcid.org/0000-0003-4206-4339)
- Ziyi Guo (ORCID: https://orcid.org/0000-0002-0324-7389)
- Yu-Tong Mei
- Dan Yang (ORCID: https://orcid.org/0000-0001-9984-7225)
Institutions
- 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)
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
Funders
- National Natural Science Foundation of China
- Fundamental Research Funds of China West Normal University