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Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone ?,?-Vicinal Difunctionalization.

ABSTRACT: The telescoping of allyl-palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts. The compatibility of the dehydrogenation conditions additionally allows for efficient trapping of the intermediate enolate with various electrophiles. The utility of this approach is demonstrated by comparison to several previously reported multistep sequences.

SUBMITTER: Chen Y

PROVIDER: S-EPMC5884112 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization.

Chen Yifeng Y Huang David D Zhao Yizhou Y Newhouse Timothy R TR

Angewandte Chemie (International ed. in English) 20170613 28

The telescoping of allyl-palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts. The compatibility of the dehydrogenation conditions additionally allows for efficient trapping of the intermediate enolate with various electrophiles. The utility of this approach ...[more]

PMID: 28561999

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