Journal
ORGANIC LETTERS
Volume 19, Issue 9, Pages 2294-2297Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00839
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Funding
- National Natural Science Foundation of China (NSFC) [21572047]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [15IRTSTHN003]
- Program for Science and Technology Innovation Talents in Universities of Henan Province [15HASTIT005]
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An unprecedented Rh(III)-catalyzed double C(sp(2)) H bond carbenoid insertion and animlation of 2-aryl-3-cyanopyridines with alpha-diazo carbonyl compounds is presented. Through this cascade reaction, a series of naphthoquinolizinone derivatives with a large pi-system were efficiently prepared. The reactions could selectively afford naphthoquinolizinones with either an amine or an amide unit attached on the 11-position depending on the nature of the solvent and the additive used. Compared with literature methods, this is a more efficient, convenient, and atom-economic way to provide polycyclic heteroaromatic compounds through direct pi-extension of simple aromatics via inert C-H bond activation and functionalization.
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