Journal article
Yang Yang, Peng Liu
ACS Catalysis, vol. 5, 2015, pp. 2944-2951
ACS Catalysis, vol. 5, 2015, pp. 2944-2951
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APA
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Yang, Y., & Liu, P. (2015). 55. Mechanism and Origins of Selectivities in the Copper-Catalyzed Dearomatization-Induced ortho C–H Cyanation of Vinylarenes. ACS Catalysis, 5, 2944–2951. https://doi.org/10.1021/acscatal.5b00443
Chicago/Turabian
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Yang, Yang, and Peng Liu. “55. Mechanism and Origins of Selectivities in the Copper-Catalyzed Dearomatization-Induced Ortho C–H Cyanation of Vinylarenes.” ACS Catalysis 5 (2015): 2944–2951.
MLA
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Yang, Yang, and Peng Liu. “55. Mechanism and Origins of Selectivities in the Copper-Catalyzed Dearomatization-Induced Ortho C–H Cyanation of Vinylarenes.” ACS Catalysis, vol. 5, 2015, pp. 2944–51, doi:10.1021/acscatal.5b00443.
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@article{yang2015a,
title = {55. Mechanism and Origins of Selectivities in the Copper-Catalyzed Dearomatization-Induced ortho C–H Cyanation of Vinylarenes},
year = {2015},
journal = {ACS Catalysis},
pages = {2944-2951},
volume = {5},
doi = {10.1021/acscatal.5b00443},
author = {Yang, Yang and Liu, Peng}
}
The mechanism of the copper-catalyzed regioselective ortho C–H cyanation of vinylarenes has been investigated using density functional theory calculations. This C–H cyanation is composed of two discrete catalytic cycles (the copper-catalyzed electrophilic cyanative dearomatization and the subsequent base-catalyzed hydrogen transposition) that furnish the ortho C–H cyanated arenes. The electrophilic cyanation step features a unique six-membered transition state, leading to the formation of the dearomatized intermediate with a high level of site selectivity. Such dearomatization significantly increases the reactivity of the C–H bond, thereby enabling the base-assisted C–H activation in the following steps.
