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Radical addition of ketones and cyanide to olefins via acid catalyzed formation of intermediate alkenyl peroxides

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Shao,  Wen
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Lux,  Marcel
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Klussmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Shao, W., Lux, M., Breugst, M., & Klussmann, M. (2019). Radical addition of ketones and cyanide to olefins via acid catalyzed formation of intermediate alkenyl peroxides. Organic Chemistry Frontiers, 6(11), 1796-1800. doi:10.1039/C9QO00447E.


Cite as: http://hdl.handle.net/21.11116/0000-0003-E10E-0
Abstract
A Brønsted acid catalyzed method was developed for the synthesis of γ-cyanoketones from sulfonyl cyanides, olefins and ketones. The reaction is believed to proceed via intermediate formation of alkenyl peroxides by condensation of ketones with tert-butylhydroperoxide. These unstable compounds decompose by homolytic O–O bond cleavage, generating ketone-derived radicals which add to the olefins and generate the final products after reaction with the sulfonyl cyanide, thereby forming two new C–C bonds. A range of different ketones and olefins can be used, including steroidal ketones and simple alkyl olefins. The products can be further transformed to substituted lactones and piperidines, including a tetracyclic one. This reaction can thus be utilized to gain access to complex molecules from simple starting materials in only a few synthetic steps.