Copper nanocrystal plane effect on stereoselectivity of catalytic deoxygenation of aromatic epoxides

Journal of the American Chemical Society
Bin XiaoYadong Li

Abstract

Previous studies have shown that crystal planes of heterogeneous catalysts could display enhanced activity, such that higher turnover or chemoselectivity could be achieved. Here we report an example where the reaction stereoselectivity was significantly affected by the catalyst crystal planes. In copper-catalyzed deoxygenation reaction of aromatic epoxides, copper cubes, wires, and plates gave the olefin products with different cis/trans selectivities, whereas homogeneous copper catalysts showed poor selectivity. Scanning tunneling microscope and density functional theory studies revealed that the different adsorption mode and higher adsorption strength of epoxide oxygen on Cu{100} plane were responsible for the observed variation of selectivity. The copper-catalyzed deoxygenation reaction provided new practical access to cis-olefins from readily available aromatic epoxides. Our work also indicated that nanocrystal catalysts may provide useful stereochemical control in organic reactions.

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Citations

Oct 27, 2015·Journal of the American Chemical Society·Menglin WangJie Zeng
Feb 16, 2016·Physical Chemistry Chemical Physics : PCCP·Bang-Bao ChenShao-Ming Huang
Jun 30, 2015·Chemical Communications : Chem Comm·Xiaojing ZhaoNanfeng Zheng
Jun 3, 2020·Chemistry : a European Journal·Theo MaulbetschDoris Kunz
Jun 10, 2015·Advanced Science·Bing Ni, Xun Wang
Apr 10, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Kristen A FichthornBenjamin J Wiley
Apr 20, 2021·The Journal of Physical Chemistry. B·Tianyu Yan, Kristen A Fichthorn
Jan 11, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Daisuke Takajo, Koichi Sudoh
Apr 4, 2020·Chemical Reviews·Shufang JiYadong Li

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