Electrophotochemical Ce-Catalyzed Ring-Opening Functionalization of Cycloalkanols under Redox-Neutral Conditions: Scope and Mechanism
Zhaoliang Yang, Dali Yang, Jianye Zhang, Chenyu Tan, Jiajun Li, Shengchun Wang, Heng Zhang, Zhiliang Huang* and Aiwen Lei*
*The Institute for Advanced Studies (IAS), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, Hubei, P. R. China,
Email: zlhuang
whu.edu.cn, aiwenleiwhu.edu.cn
Z. Yang, D. Yang, J. Zhang, C. Tan, J. Li, S. Wang, H. Zhang, Z. Huang, A. Lei, J. Am. Chem. Soc., 2022, 144, 13006-13017.
DOI: 10.1021/jacs.2c05520
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Abstract
Electrophotochemical cerium catalysis enables a versatile redox-neutral method for the ring-opening functionalization of cycloalkanols. The reaction tolerates a broad range of functional groups. Even in the presence of chloride as a counteranion and electrolyte, this protocol selectively leads to the formation of C-CN, C-C, C-S, or C-oxime bonds instead of a C-halide bond after β-scission.
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proposed mechanism
Key Words
nitriles, photochemistry, electrochemistry
ID: J48-Y2022
