Synthesis of 4-Arylpiperidines from 1-Benzyl-4-piperidone:  Application of the Shapiro Reaction and Alkenylsilane Cross-Coupling

1-Benzyl-3,4-unsaturated-4-piperidinyl benzyldimethylsilane has been prepared and observed to readily undergo palladium-catalyzed cross-coupling reactions with a variety of aryl iodides and aryl bromides to generate 3,4-unsaturated 4-arylpiperidines, often at ambient temperature.

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 8; pp. 1505 - 1508
Main Authors Morrill, Christie, Mani, Neelakandha S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.04.2007
Amer Chemical Soc
Subjects
Benzyl Compounds - chemistry
Bromides - chemistry
Chemistry
Chemistry, Organic
Cross-Linking Reagents - chemistry
Molecular Structure
Physical Sciences
Piperidines - chemical synthesis
Piperidines - chemistry
Piperidones - chemistry
Science & Technology
Silanes - chemistry
POTENT
DESIGN
TETRAHYDROPYRIDINES
REAGENTS
INHIBITORS
ANTAGONISTS
DERIVATIVES
DISCOVERY
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Summary:1-Benzyl-3,4-unsaturated-4-piperidinyl benzyldimethylsilane has been prepared and observed to readily undergo palladium-catalyzed cross-coupling reactions with a variety of aryl iodides and aryl bromides to generate 3,4-unsaturated 4-arylpiperidines, often at ambient temperature.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol070241c