Dan Yang*, Yu-Tong Mei, Zi-Yi Guo, Qiu-Yao Hou, Hui Zhang, Yu-Xuan Zheng, Lin-Hai Jing*, De-Jun Cheng and Ming-Song Shi*,
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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(sp3)–C(sp3) 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.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.