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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Published in | Journal of molecular catalysis. A, Chemical Vol. 246; no. 1; pp. 231 - 236 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
Amsterdam
Elsevier B.V
01.03.2006
Elsevier |
Subjects | |
Online Access | Get full text |
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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. |
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ISSN: | 1381-1169 1873-314X |
DOI: | 10.1016/j.molcata.2005.11.009 |