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Computational study on the Rh‐catalyzed CC activation of cyclopropanol to construct diketone or monoketone
Author(s) -
Liu Tao,
Wang Ping,
Ren Hong
Publication year - 2021
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.26438
Subject(s) - selectivity , catalysis , diketone , chemistry , density functional theory , hydride , medicinal chemistry , computational chemistry , organic chemistry , hydrogen
Abstract The mechanisms of CC activation of 1‐benzylcyclopropan‐1‐ol to produce 1,6‐diketone have been investigated by density functional theory calculations. The catalyst [Cp*RhCl 2 ] 2 and additive Ag 2 CO 3 play an important role in controlling the selectivity. By using [Cp*RhCl 2 ] 2 as the catalyst and Ag 2 CO 3 as the additive, the product is 1,6‐diketone, whereas the β ‐hydride elimination product could not be obtained. The product would become monoketone in the absence of [Cp*RhCl 2 ] 2 . In addition, the combination of catalyst [Cp*RhCl 2 ] 2 and additive AgOAc would also lead to monoketone. The observed selectivity could be attributed to the electronic effect.