184226-80-0Relevant articles and documents
C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines
Brasche, Gordon,Buchwald, Stephen L.
, p. 1932 - 1934 (2008/12/22)
(Chemical Equation Presented) Copper closes the ring: Benzimidazoles are synthesized from amidines through a copper-catalyzed C-H functionalization/ C-N bond-forming process. The method tolerates a broad range of functional groups and provides the benzimidazoles in up to 89% yield. Best results are obtained by using 15 mol% Cu(OAc)2, 2-5 equivalents of HOAc as additive, and oxygen as the stoichiometric reoxidant (see scheme).
Reductive tert-butylation of anils by tert-butylmercury halides
Russell, Glen A.,Wang, Lijuan,Rajaratnam, Ragine
, p. 8988 - 8991 (2007/10/03)
tert-Butyl radicals add to the carbon atom of benzylideneanilines to form anilino radicals, which are protonated in the presence of PTSA or NH4+ in Me2SO. Reduction of the resulting aniline radical cations occurs readily by the ate complex, t-BuHgI2. In the absence of a proton donor, f-BuHgI will also transfer a hydrogen atom to the anilino radical to give the reductive alkylation product. Protonation can promote a free radical chain process involving electron transfer by substrate activation and/or by increasing the electron affinity of the intermediate radicals. Since the adduct radicals formed from benzylideneanilines are more easily protonated than the parent Schiff bases, PTSA but not NH4+ demonstrates substrate activation, although both proton donors promote the free radical reaction.
