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

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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.

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

Document Type: Research Article

Affiliations: Parco d'Orleans II Ed. 17, V.le delle Scienze. 90128 Palermo Italy.

Publication date: 2006-02-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
    The journal is essential reading for all organic chemists both in academia and industry.
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