期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 18, 期 40, 页码 12873-12879出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201201862
关键词
C-H activation; C-C coupling; oxidation; reaction mechanisms; ruthenium
资金
- NSFC [21072097, 21072101]
- SRFDP [20110031110009]
The mechanism of [{RuCl2-(p-cymene)}(2)]-catalyzed oxidative annulations of isoquinolones with alkynes was investigated in detail. The first step is an acetate-assisted C-H bond activation process to form cyclometalated compounds. Subsequent mono-alkyne insertion of the Ru-C bonds of the cyclometalated compounds then takes place. Finally, oxidative coupling of the C-N bond of the insertion compounds occurs to afford Ru-0 sandwich complexes that undergo oxidation to regenerate the catalytically active Ru-II complex with the copper oxidant and release the desired dibenzo[a,g]quinolizin-8-one derivatives. All of the relevant intermediates were fully characterized and determined by single crystal X-ray diffraction analysis. The [{RuCl2(p-cymene)}(2)]-catalyzed C-H bond functionalization of isoquinolones with alkynes to synthesize dibenzo[a,g]quinolizin-8-one derivatives through C-H/N-H activation was also demonstrated.
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