De, Pinaki Bhusan ; Pradhan, Sourav ; Punniyamurthy, Tharmalingam (2017) Stereoselective copper-catalyzed cross-coupling of aziridines with benzimidazoles via nucleophilic ring opening and C(sp2)–H functionalization The Journal of Organic Chemistry, 82 (6). pp. 3183-3191. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b0026...
Related URL: http://dx.doi.org/10.1021/acs.joc.7b00265
Abstract
A 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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 106975 |
| Deposited On: | 22 Jun 2017 09:57 |
| Last Modified: | 22 Jun 2017 09:57 |
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