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Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to ?-cyano ketone.

ABSTRACT: A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented "cyano-borrowing reaction" has been developed. Cleavage of the C-CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to ?,?-unsaturated ketones proceeded to deliver a range of racemic ?-cyano ketones with good to high yields. The practical procedure with the use of a commercial and less-toxic CN source bodes well for wide application of this protocol.

SUBMITTER: Li ZF 

PROVIDER: S-EPMC6568282 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone.

Li Zhao-Feng ZF   Li Qian Q   Ren Li-Qing LQ   Li Qing-Hua QH   Peng Yun-Gui YG   Liu Tang-Lin TL  

Chemical science 20190506 22

A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones <i>via</i> an unprecedented "cyano-borrowing reaction" has been developed. Cleavage of the C-CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturated ketones proceeded to deliver a range of racemic β-cyano ketones with good to high yields. The practical procedure with the use of a commercial and less-toxic CN source bodes well for wide ap  ...[more]

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