Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 7, Pages 3471-3479Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00059
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Funding
- National Natural Science Foundation of China [21272231, 21402190, 21472186]
- Dalian Institute of Chemical Physics, Chinese Academy of Sciences
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Rh(III)-catalyzed C-H activation of 2-phenylimidazo[1,2-alpha]pyridines in divergent oxidative coupling with alkynes has been achieved. Selective mono versus 2-fold C-H activation has been attained under condition control. When AgOAc was used as an oxidant, the coupling afforded 5,6-disubstituted naphtho[1 ',2 ':4,5]imidazo[1,2-alpha]pyridines as a result of initial nitrogen chelation-assisted C-H activation at the benzene ring followed by rollover C-H activation. In contrast, the reaction afforded a fused isoquinolinium salt as a result of C-C and C-N coupling when AgBF4 was employed as a co-oxidant. A rhodacyclic intermediate has been isolated.
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