Photochemical synthesis of N-adamantylhomoallylamines through addition of cyclic olefins to imines catalyzed by alumina grafted cadmium sulfide.

Aldemir M, Heinemann FW, Kisch H (2012)


Publication Status: Published

Publication Type: Journal article

Publication year: 2012

Journal

Book Volume: 11

Pages Range: 908-913

Journal Issue: 6

DOI: 10.1039/c1pp05298e

Abstract

Grafting cadmium sulfide onto alumina induces a small bandgap widening and a more significant lifetime variation of the light generated charge carriers from 0.76 microseconds measured for pristine CdS to 0.75, 0.86, and 1.20 microseconds found for CdS/Al(2)O(3) containing 30, 20, and 9% of CdS, respectively. The quasi-Fermi level of electrons of -0.42 V (NHE) is not significantly changed. These alumina grafted semiconductor photocatalysts enable the linear addition of cyclopentene, cyclohexene, and α-pinene to N-adamantylimines affording novel homoallyladamantylamines in isolated yields of 21-85% through a regioselective C-C heterocoupling of intermediate allyl and α-aminobenzyl radicals. As by-products hydrodimers of the imine are formed by C-C homocoupling of the benzylic radicals. Different from heterocoupling, the homocoupling is a stereospecific process directed by the nature of the olefin employed in the reaction.

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How to cite

APA:

Aldemir, M., Heinemann, F.W., & Kisch, H. (2012). Photochemical synthesis of N-adamantylhomoallylamines through addition of cyclic olefins to imines catalyzed by alumina grafted cadmium sulfide. Photochemical & Photobiological Sciences, 11(6), 908-913. https://doi.org/10.1039/c1pp05298e

MLA:

Aldemir, Muege, Frank Wilhelm Heinemann, and Horst Kisch. "Photochemical synthesis of N-adamantylhomoallylamines through addition of cyclic olefins to imines catalyzed by alumina grafted cadmium sulfide." Photochemical & Photobiological Sciences 11.6 (2012): 908-913.

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