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Zhu, Xiaoli; Liu, Xunshen; Xia, Fei; Liu, Lu
Molecules (Basel, Switzerland), 02/2023, Letnik: 28, Številka: 4Journal Article
The aromatic C(spsup.2)-H functionalization of unprotected naphthols with α-phenyl-α-diazoesters under mild conditions catalyzed by CuCl and CuClsub.2 exhibits high efficiency and unique ortho-selectivity. In this study, the combination of density functional theory (DFT) calculations and experiments is employed to investigate the mechanism of C-H functionalization, which reveals the fundamental origin of the site-selectivity. It explains that CuCl-catalyzed ortho-selective C-H functionlization is due to the bimetallic carbene, which differs from the reaction catalyzed by CuClsub.2 via monometallic carbene. The results demonstrate the function of favourable H-bond interactions on the site- and chemo-selectivity of reaction through stabilizing the rate-determining transition states in proton (1,3)-migration.
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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