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Synfacts 2015; 11(1): 0108
DOI: 10.1055/s-0034-1379725
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Visible-Light-Promoted aza-Henry Reaction Using Mesoporous Cu2O

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Aya Ohno
Wang J, Ma J, Li X, Li Y, Zhang G, Zhang F, Fan X * Tianjin University, P. R. of China
Cu2O Mesoporous Spheres with a High Internal Diffusion Capacity and Improved Catalytic Ability for the aza-Henry Reaction Driven by Visible Light.

Chem. Commun. 2014;
50: 14237-14240
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Publication History

Publication Date:
15 December 2014 (online)

 
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Key words

mesoporous copper(I) oxide - photocatalytic aza-Henry reaction - visible light - oxygen

Significance

Mesoporous copper(I) oxide spheres with different pore sizes (5 nm for SP-Cu2O and 15 nm for LP-Cu2O) were prepared and applied to the visible-light-promoted aza-Henry reaction. The reaction of N-aryl tetrahydroisoquinolines 1 with nitroalkanes 2 was carried out in the presence of LP-Cu2O and molecular oxygen under the irradiation of blue LEDs to afford the corresponding coupling products 3 in 83–90% yield. The reaction without catalyst gave 3a in only 5% yield under otherwise similar conditions.


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Comment

The catalysts were characterized by SEM, TEM, XRD, and N2 adsorption–desorption analyses. For the formation of 3a, LP-Cu2O was recovered by centrifugation and reused four times without significant loss of catalytic activity. SEM observation of LP-Cu2O after the fifth run showed no change of its morphology. The preparation of mesoporous Cu2O spheres with small pore size was previously reported by Shang, Zhang and Guo (J. Mater. Chem. 2012, 22, 856).


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