1199790-77-6Relevant articles and documents
Regiospecific decarboxylative allylation of nitriles
Recio III, Antonio,Tunge, Jon A.
supporting information; scheme or table, p. 5630 - 5633 (2010/03/02)
[Chemical Equation Presented] Palladium-catalyzed decarboxylative α-allylation of nitriles readily occurs with use of Pd2(dba) 3 and rac-BINAP. This catalyst mixture also allows the highly regiospecific α-allylation of nitriles in the presence of much more acidic α-protons. Thus, the reported method provides access to compounds that are not readily available via base-mediated allylation chemistries. Lastly, mechanistic investigations indicate that there is a competition between C- and N-allylation of an intermediate nitrile-stabilized anion and that N-allylation is followed by a rapid [3,3]-sigmatropic rearrangement.