Pyrrole Functionalization by Copper-Catalyzed Nitrene Transfer Reactions |
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| Authors: | Anabel M Rodríguez Manuel R Rodríguez Prof Dr M Mar Díaz-Requejo Prof Dr Pedro J Pérez |
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| Affiliation: | Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 - Huelva, Spain |
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| Abstract: | The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The Cα-H bond of 1H-pyrrole is amidated upon the formal insertion of the NTs (Ts=p-toluenesulfonyl) group catalyzed by TpBr3Cu(NCMe) (TpBr3=hydrotris(3,4,5-tribromo-pyrazolyl)borate). N-substituted pyrroles also verify the same transformation. The mechanism proposal is similar to that previously described for benzene amidation with the same catalyst and PhI=NTs, which takes place through aziridine formation, ring opening and 1,2-hydrogen shift. A cascade reaction involving the coupling of 2,5-dimethylfuran, 1,2,3-trimethyl-pyrrole and a nitrene NTs group is also described, leading to a 1,2-dihydropyridine-imine compound. |
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| Keywords: | nitrene transfer pyrrole functionalization C−H amidation copper catalysis copper nitrene |
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