N-Hydroxyphthalimide (NHPI)/Lead Tetraacetate, a Peculiar System for the Phthalimide-N-Oxyl (PINO) Radical Generation.

The development of efficient catalytic system for selective organic transformation is currently one of the challenging tasks in synthetic organic chemistry. In recent years, N-hydroxyphthalimide (NHPI) has been recognized as a valuable catalyst for the aerobic oxidation of various organic compounds under mild conditions. The generation of the phthalimide-N-oxyl (PINO) radicals from its precursor NHPI, can be achieved by using different ways including electrochemical, enzymatic and chemical methods. Among all of these methods, the use of lead tetraacetate for the PINO radicals' generation seems to be the most peculiar, several kinetic and mechanistic “anomalies” for this catalytic system being reported.