期刊
ACS CATALYSIS
卷 9, 期 5, 页码 4179-4188出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b00832
关键词
nitroxyl radical catalysis; pyridines; redox reaction; iminyl radical; enones; annulation
资金
- National Natural Science Foundation of China [21873041, 21632001, 21422205]
- 111 project
- Program for Changjiang Scholars and Innovative Research Team in University [IRT-15R28]
- Fundamental Research Funds for the Central Universities [lzujbky-2016-ct02, lzujbky-2016-ct08]
A 4-HO-TEMPO-catalyzed redox strategy for the synthesis of pyridines through the annulation of cyclopropanols and oxime acetates has been developed. This protocol features good functional group tolerance and high chemoselectivity and also promises to be efficient for the late-stage functionalization of skeletons of drugs and natural products. Mechanism studies indicate that the reaction involves the in situ generated alpha,beta-unsaturated ketones and imines as the key intermediates, which are derived from cyclopropanols and oxime acetates via a TEMPO/TEMPOH redox cycle, respectively. The pyridine products are formed as a result of annulation of enones with imines followed by TEMPO-catalyzed oxidative aromatization by excess oxime acetates. This method not only realizes the TEMPO-catalyzed redox reaction but also broadens the frontiers for TEMPO in catalysis.
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