33650-06-5Relevant articles and documents
An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride
Nakayama, Yuji,Yokoyama, Naota,Nara, Hideki,Kobayashi, Tohru,Fujiwhara, Mitsuhiko
, p. 2322 - 2330 (2015)
An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.