Highly Regioselective Palladium-Catalyzed Internal Arylation of Allyltrimethylsilane with Aryl Triflates

Highly regioselective ligand-controlled Heck-arylation reactions of allyltrimethylsilane, delivering branched β-products, were performed in moderate to good yields. The high preference for internal over terminal double-bond arylation suggests a contribution from the β-cation-stabilizing effect of si...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 63; no. 15; pp. 5076 - 5079
Main Authors Olofsson, Kristofer, Larhed, Mats, Hallberg, Anders
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.07.1998
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENOL ETHERS
ONE-POT SYNTHESIS
COUPLING REACTIONS
CARBENIUM IONS
PHOSPHINE LIGAND
STEREOCHEMICAL ASPECTS
ORGANIC HALIDES
ALLYLSILANES
HECK REACTION
GRIGNARD-REAGENTS
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Summary:Highly regioselective ligand-controlled Heck-arylation reactions of allyltrimethylsilane, delivering branched β-products, were performed in moderate to good yields. The high preference for internal over terminal double-bond arylation suggests a contribution from the β-cation-stabilizing effect of silicon. Microwave-promoted palladium-catalyzed coupling reactions proceeded with the same regioselectivity in six entries out of eight with the reaction times cut sharply down to 5−10 min.
Bibliography:ark:/67375/TPS-H1MWS3VH-F
istex:79DF7BF387A5DCF062B2D82DDFE1D04EBFC4C427
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo980249n