期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2021, 期 2, 页码 266-273出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001270
关键词
Alkyne insertion; Annulation; Decarbonylation; DFT calculations; Ruthenium
资金
- National Natural Science Foundation of China [21873055, 21702119, 21903048]
- Natural Science Foundation of Shandong Province [ZR2019MB016, ZR2017QB001]
- High Performance Computing Center of Qufu Normal University
Density functional theory calculations were used to explore the Ru-catalyzed decarbonylative annulation reaction, revealing a Ru(II)-Ru(0)-Ru(II) transformation. The oxidative addition of C(carbonyl)-C(carbonyl) bond to Ru(0) was found to be favorable, while the regeneration of the catalyst was predicted to be achieved by the oxidation of air oxygen. This study provides new insights into the decarbonylative annulation.
Density functional theory calculations have been performed to explore the Ru-catalyzed decarbonylative annulation reaction of 3-hydroxy-2-phenyl-chromone with an alkyne to synthesize spiroindenebenzofuranones. A Ru(II)-Ru(0)-Ru(II) rather than a Ru(II)-Ru(IV)-Ru(II) transformation was found involved in the decarbonylation process, which is responsible for the sequence of alkyne insertion/decarbonylation. Oxidative addition of C(carbonyl)-C(carbonyl) bond to Ru(0) and the Ru(II)-C(sp(2)) bond formation were confirmed to be favorable for the decarbonylation, meanwhile oxidative addition of C(carbonyl)-C(carbonyl) bond to Ru(0) is likely to be the rate-determining step for the entire catalytic cycle. It is predicted that the regeneration of the catalyst was achieved by the oxidation of air oxygen in the absence of other oxidants. The current theoretical study provides new insights into the decarbonylative annulation.
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