Copper
or silver-catalyzed direct C(sp2)–H/N–H
electrochemical cross-coupling of phthalimide and heterocyclic arenes
(2-phenylpyridine, benzo[h]quinoline, benzoxazole,
and benzothiazole, etc.) for the efficient synthesis of phthalimide
derivatives is described. This reaction features good yield, mild
conditions, and broad substrate scope, which provides an efficient
and straightforward protocol to access this type of tertiary amines.
For the first time, the proposed protocol is based not only on a copper
catalyst but also on silver, which has never been used for this purpose
before, and both give comparable results. Mechanistic investigations
(voltammetry, ESR studies) disclosed that a free-radical pathway might
be excluded in this process accomplished through Cu(I)/Cu(II)/Cu(III)
or Ag(I)/Ag(III) cycles.