Highly efficient Barbier allylation from allyl alcohol using iridium(I)/tin(II): Unusual and indirect roles of allyl alcohol and tin

Facile one-carbon homologation of allyl alcohol to homoallyl alcohol using Ir I–SnCl 2 as reagent is described, which might involve the intermediacy of a π-allyl-iridium intermediate. ▪ A reagent combination of SnCl 2 and catalytic [Ir(COD)Cl] 2 (1 mol%) in THF–H 2O promotes the reaction of allyl al...

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Bibliographic Details
Published inJournal of molecular catalysis. A, Chemical Vol. 246; no. 1; pp. 231 - 236
Main Authors Banerjee, Moloy, Roy, Sujit
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier B.V 01.03.2006
Elsevier
Subjects
Allyl transfer
Barbier allylation
Catalysis
Chemistry
Diallyl ether
Exact sciences and technology
General and physical chemistry
Homoallylic alcohol
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
π-Allyl-iridium
Diallyl ether
π-Allyl-iridium
Homoallylic alcohol
Allyl transfer
Barbier allylation
Ether
Platinoid Complexes
Transition metal Complexes
Iridium Complexes
Allylation
Tin Chlorides
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Summary:Facile one-carbon homologation of allyl alcohol to homoallyl alcohol using Ir I–SnCl 2 as reagent is described, which might involve the intermediacy of a π-allyl-iridium intermediate. ▪ A reagent combination of SnCl 2 and catalytic [Ir(COD)Cl] 2 (1 mol%) in THF–H 2O promotes the reaction of allyl alcohol and aldehyde leading to homoallyl alcohols in good to excellent yields. Control studies suggest the plausible participation of π-allyl-iridium intermediate(s) from which direct allyl transfer takes place to aldehyde.
ISSN:1381-1169
1873-314X
DOI:10.1016/j.molcata.2005.11.009