Ligated Regioselective Pd-II Catalysis to Access beta-Aryl-Bearing Aldehydes, Ketones, and beta-Keto Esters

By employing ligands in the PdII-mediated arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks beta-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalitie...

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Bibliographic Details
Published inEuropean journal of organic chemistry Vol. 2012; no. 25; pp. 4694 - 4698
Main Authors Vellakkaran, Mari, Andappan, Murugaiah M. S., Kommu, Nagaiah
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.09.2012
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIME-DERIVED PALLADACYCLES
BASE-FREE
ARYLATION
Palladium
INTERMOLECULAR HECK REACTION
FLAVONOIDS
Dihydrochalcones
HIGHLY EFFICIENT
Allylic compounds
ss-Aryl carbonyl compounds
Homogeneous catalysis
Arylboronic acids
ALLYL ALCOHOLS
ANTIVIRAL ACTIVITY
IONIC LIQUIDS
DERIVATIVES
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Summary:By employing ligands in the PdII-mediated arylative isomerization of allyl alcohols, a milder and regioselective access to the versatile building blocks beta-aryl aldehydes and ketones was developed. This new and chelation-controlled protocol enabled the compatibility of wide range of functionalities to generate dihydrochalcones, a-benzyl-a'-alkyl acetones, dihydrocinnamaldehydes, and a-benzyl beta-keto esters (from BaylisHillman adducts). A practical multigram synthesis of an intermediate for Propafenone was also demonstrated.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200770