[Investigation of the Aqueous Transmetalation of π-Allylpalladium with Indium: Some Theoretical and Experimental Evidence About the Nature of Allylindium Intermediates ]

Author(s): Francesco Ferrante, Gianfranco Fontana, Giuseppe Savona

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 2 , 2006


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Abstract:

In this paper we report some theoretical and experimental evidence concerning the nature of the allyl-In intermediate generated by umpolung of allyl-Pd complexes in the Pd(OAc)2/TPPTS catalysed allylation reaction of benzaldehyde. The allylic substrate reacts at the substituted terminus, because of the formation of an equilibrating mixture of η1-allyl-In(I) specie with the γ-substituted regioisomer being more reactive.

Keywords: allyl-indium, allyl-palladium, umpolung, Allylation

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Article Details

VOLUME: 3
ISSUE: 2
Year: 2006
Page: [98 - 102]
Pages: 5
DOI: 10.2174/157017806775224305
Price: $65

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