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Allyl‐Palladium‐Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β‐Vicinal Difunctionalization
Author(s) -
Chen Yifeng,
Huang David,
Zhao Yizhou,
Newhouse Timothy R.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201704874
Subject(s) - ketone , enone , dehydrogenation , electrophile , chemistry , aryl , catalysis , palladium , nucleophile , allylic rearrangement , alkene , organic chemistry , alkyl , combinatorial chemistry
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.