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Bioinspired Iron-Catalyzed Dehydration of Aldoximes to Nitriles: A General N-O Redox-Cleavage Method

Hongjie Gao, Jia-Yi Chen, Zhiqiang Peng, Lei Feng, Chen-Ho Tung and Wenguang Wang*

*College of Chemistry, Beijing Normal University, Beijing 100875, China, Email: wwgbnu.edu.cn

H. Gao, J.-Y. Chen, Z. Peng, L. Feng, C.-H. Tung, W. Wang, J. Org. Chem., 2022, 87, 10848-10857.

DOI: 10.1021/acs.joc.2c01122


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Abstract

Cp*Fe(1,2-Cy2PC6H4O) rapidly converts various aliphatic and aromatic aldoximes to nitriles with release of H2O at room temperature. This iron-catalyzed acceptorless dehydration approach represents a general method for the preparation of nitriles, and it also delivers salicylonitriles by catalyzing the Kemp elimination reaction.


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proposed mechanism



Key Words

nitriles


ID: J42-Y2022