A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones 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 application of this protocol.
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| http://dx.doi.org/10.1039/c9sc00640k | DOI Listing |
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School of Chemistry and Chemical Engineering , Southwest University, Chongqing 400715 , China . Email: ; Email:
A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones 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 application of this protocol.
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