Cationic Iridium Complex-Catalyzed Intermolecular Hydroalkylation of Unactivated Alkenes with 1,3-Diketones

Intermolecular hydroalkylation of unactivated terminal alkenes with 1,3-diketones under neutral conditions has been achieved using a cationic iridium catalyst. An active C–H bond of 2,4-pentadione (2a) added to 1-octene (1a) under refluxing DCE to give a Markovnikov product in 88% yield. A broad sco...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 3; pp. 741 - 744
Main Authors Takeuchi, Ryo, Sagawa, Jun, Fujii, Masaki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.02.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
MECHANISM
ALPHA,OMEGA-DIYNES
PLATINUM(II)
OLEFINS
INTRAMOLECULAR HYDROALKYLATION
ASSISTED ALKYLATION
BETA-KETO-ESTERS
2+2+2 CYCLOADDITION
STABILIZED CARBON NUCLEOPHILES
DIYNES
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Summary:Intermolecular hydroalkylation of unactivated terminal alkenes with 1,3-diketones under neutral conditions has been achieved using a cationic iridium catalyst. An active C–H bond of 2,4-pentadione (2a) added to 1-octene (1a) under refluxing DCE to give a Markovnikov product in 88% yield. A broad scope of alkenes and 1,3-diketones was observed. The products were easily converted to heterocycles. This reaction provides a new method for extending a carbon chain from an unactivated aliphatic terminal alkene.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b03975