Hydride Shift Initiated Reaction Cascades D = Donor,
Hydride Shift Initiated Reaction Cascades
D = Donor, A = Acceptor
An intramolecular hydride shift generates an electrophile/nucleophile pair that recombines in a bond forming,
complexity enhancing event. Common donors are tertiary N-atoms due to their ability to stabilize a positive
charge. Iminium ions and alkylidene malonates are good acceptor moieties for these processes. The
overall sequence leads to the redox neutral functionalization of relatively unreactive CH bonds.
Best conditions for aromatic amines:
EtOH, CF3SO3H (0.2 equiv), reflux.
Best conditions for aliphatic amines:
EtOH, CF3COOH (1.2 equiv), reflux.
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