jo7b00265_si_001.cif (337.77 kB)
Stereoselective Copper-Catalyzed Cross-Coupling of Aziridines with Benzimidazoles via Nucleophilic Ring Opening and C(sp2)–H Functionalization
dataset
posted on 2017-02-24, 00:00 authored by Pinaki
Bhusan De, Sourav Pradhan, Tharmalingam PunniyamurthyA copper-catalyzed
cross-coupling of 2-alkyl-/2-arylaziridines
with benzimidazoles is reported. The reactions involve a regiospecific
ring opening of aziridines with benzimidazoles to give benzoimidazolylethylamine
derivatives that lead to dehydrogenative cross-coupling between C(sp2)-H and N–H bonds to produce dihydroimidazobenzimidazoles.
Optically active 2-arylaziridines can be stereoinvertivebly cross-coupled
with high enantiomeric purities (77–97% ee). These aerobic
catalytic systems comprise an inexpensive Cu(II) salt and PCy3 ligand at moderate temperature.
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2- arylaziridineseestereoinvertivebly cross-coupledFunctionalizationbenzimidazoleOpticallydehydrogenative cross-couplingpuritieregiospecific ring openingStereoselective Copper-Catalyzed Cross-CouplingenantiomericCudihydroimidazobenzimidazolebenzoimidazolylethylamine derivativesPCy 3 ligandcopper-catalyzed cross-couplingAziridinealkylNucleophilic RingBenzimidazolebond
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