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Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes.

ABSTRACT: Described are several classes of unusual or unprecedented carbonyl-ene-type reactions, including those between alpha olefins and aromatic aldehydes. Catalyzed by nickel, these processes complement existing Lewis acid-catalyzed methods in several respects. Not only are monosubstituted alkenes, aromatic aldehydes, and tert-alkyl aldehydes effective substrates, but monosubstituted olefins also react faster than those that are more substituted, and large or electron-rich aldehydes are more effective than small or electron-poor ones. Conceptually, in the presence of a nickel-phosphine catalyst, the combination of off-the-shelf alkenes, silyl triflates, and triethylamine functions as a replacement for an allylmetal reagent.

SUBMITTER: Ho CY

PROVIDER: S-EPMC3148195 | biostudies-literature | 2006 Apr

REPOSITORIES: biostudies-literature

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Nickel-catalyzed, carbonyl-ene-type reactions: selective for alpha olefins and more efficient with electron-rich aldehydes.

Ho Chun-Yu CY Ng Sze-Sze SS Jamison Timothy F TF

Journal of the American Chemical Society 20060401 16

Described are several classes of unusual or unprecedented carbonyl-ene-type reactions, including those between alpha olefins and aromatic aldehydes. Catalyzed by nickel, these processes complement existing Lewis acid-catalyzed methods in several respects. Not only are monosubstituted alkenes, aromatic aldehydes, and tert-alkyl aldehydes effective substrates, but monosubstituted olefins also react faster than those that are more substituted, and large or electron-rich aldehydes are more effective ...[more]

PMID: 16620106

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