期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 5, 页码 2542-2555出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02948
关键词
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资金
- Natural Science Foundation of China [21390400, 21572232, 21521002]
- Chinese Academy of Science [QYZDJ-SSW-SLH023]
- National Program of Top-notch Young Professionals
We report herein our mechanistic studies of the ortho-quinone-catalyzed aerobic oxidation of primary, secondary, and tertiary amines. Two different catalytic pathways were discovered for the reductive half reactions: for primary amines, the reaction was found to proceed via a transamination pathway, while the reactions with secondary amines and tertiary amines proceeded via hydride transfer. We also found that the amine substrates could significantly promote the regeneration of the ortho-quinone catalyst in the oxidative half reaction, in which a proton transfer occurs between the amine substrates and catechol derivatives (the reduced form of the ortho-quinone catalyst).
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