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Published on: November 21, 2017
Oxidative Amination Ring Cleavage of Catechols for Muconic Acid Mononitriles
Jianwei Yan1, Yiwan Jiang1, Xiaobing Li1
1School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, P. R. China.
None:
An efficient oxidative ring-opening reaction of catechols to afford cis,cis-muconic acid mononitriles was established under mild conditions with a broad substrate scope. The transformation enables most catechols containing asymmetric substituents to generate a single or major product. The reaction can be scaled to gram quantities, highlighting its practical utility. Experimental studies and density functional theory calculations support a mechanism involving pyrocatechol oxidation, quinone-amine condensation, nucleophilic addition, and subsequent aromatic ring cleavage.
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