Palladium-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions

A protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates has been developed using a Pd/Q-Phos catalyst. Efficient intermolecular coupling of a variety of ketones with alkenyl bromides was achieved with a slight excess of LiHMDS and temperatures down to 0 °C.

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Bibliographic Details
Published inOrganic letters Vol. 16; no. 15; pp. 3970 - 3973
Main Authors Grigalunas, Michael, Ankner, Tobias, Norrby, Per-Ola, Wiest, Olaf, Helquist, Paul
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.08.2014
Amer Chemical Soc
Subjects
Alkenes - chemical synthesis
Alkenes - chemistry
Catalysis
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Hydrocarbons, Brominated - chemistry
INTERMOLECULAR ALPHA-ARYLATION
Ketones - chemical synthesis
Ketones - chemistry
LIGAND
Molecular Structure
Organic
Organic Chemistry
Organisk kemi
OXINDOLES
Palladium - chemistry
Physical Sciences
RATE ACCELERATION
Science & Technology
VINYL HALIDES
OXINDOLES
RATE ACCELERATION
LIGAND
VINYL HALIDES
INTERMOLECULAR ALPHA-ARYLATION
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Summary:A protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates has been developed using a Pd/Q-Phos catalyst. Efficient intermolecular coupling of a variety of ketones with alkenyl bromides was achieved with a slight excess of LiHMDS and temperatures down to 0 °C.
Bibliography:National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol5017965