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Electrochemical cleavage of allyl aryl ethers and allylation of carbonyl compounds: umpolung of allyl-palladium species

✍ Scribed by D. Franco; D. Panyella; M. Rocamora; M. Gomez; J.C. Clinet; G. Muller; E. Duñach

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
214 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

The electrochemical, Pd-catalyzed cleavage of the C-O bond of allyl aryl ethers has been examined; the method constitutes a new alternative for allyl ether deprotection. The allyl transfer from the allyl ether to the carbonyl group in 2-allyloxy benzaldehydes is reported and is an example of allyl-Pd reactivity umpolung. Pd(II) complexes, associated to several nitrogen ligands are efficient catalyst precursors for these electrochemical reactions.

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for their generous supply of ligands 24 and 10, 14, and 15, respectively. We are indebted to Corrado Sangermani and Gloria Borin for their synthetic expertise and contributions. Special thanks go to Maurizio Franzini for his advice. This work was supported by the University of Pavia (Progetto Giovan