Organic Letters
Letter
(13) As suggested by one of the referees, N-vinylphthalimide and
methyl acrylate were reacted under the optimized reaction conditions
with benzene obtaining the corresponding 1,1-diarylated products
confirming that the N-Phth group does not serve as a chelation
auxiliary neither to assist palladium in the activation of terminal C−H
bond of olefin nor to explain the sole Z stereoproduct. The role of the
N-Phth group on substrates/products is to block both hydrogens. In
addition, it is stable under the acidic/oxidative reaction conditions and
it allows strong bases or acids to be avoided in the deprotection step.
(14) For recent use of dehydroalanines in Friedel-Craft-Michael-type
addition, see: (a) Righi, M.; Bartoccini, F.; Lucarini, S.; Piersanti, G.
Tetrahedron 2011, 67, 7923−7928. (b) Bartolucci, S.; Bartoccini, F.;
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(d) Mari, M.; Lucarini, S.; Bartoccini, F.; Piersanti, G.; Spadoni, G.
Beilstein J. Org. Chem. 2014, 10, 1991−1998. (e) Rossi, E.; Negrato,
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2006.
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