178889-49-1Relevant articles and documents
Catalytic acryloxypalladation of vinylcycloalkanes and exo-methylene cycloalkanes. Mechanistic insights into the competition between allylic acryloxypalladation and formation of a-methylene y-butyrolactones
Ferret, Nicolas,Mussate-Mathieu, Laurence,Perfetti, Patricia,Zahra, Jean-Pierre,Waegell, Bernard
, p. 1023 - 1031 (2007/10/03)
Acryloxypalladation of ezo-methylenecycloalkanes (three-, four-, five- and six-membered rings) and vinylcycloalkanes (three-, five- and six-membered rings) in the presence of the Pd(OAc)2/p-benzoquinone/MnC>2 catalytic system is reported. Except for the case of eio-methylenecyclopropane, this reaction provides a rapid entry to the corresponding Q-metliylene -/-butyrolactone, which essentially results from a 1,2-Markovnikov acryloxypalladation addition on the double bond. The subsequent insertion of the acrylate double bond into the carbon-palladium bond is followed by a β-elimination step. However, this reaction competes with the formation of intermediate -allyl complexes which yields the corresponding allylic acrylates. The ratio of butyrolactones to allylic acrylates is dependent on ring size. Elsevier,.