RT Journal Article
T1 Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
A1 Moreno Rodríguez, Anabel
A1 Ramírez Rodríguez, Manuel
A1 Díaz Requejo, María Mar
A1 Pérez Romero, Pedro José
AB 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.
PB Wiley-VCH Verlag
SN 0021-2148
SN 1869-5868 (electrónico)
YR 2020
FD 2020-03
LK http://hdl.handle.net/10272/19698
UL http://hdl.handle.net/10272/19698
LA eng
NO Rodríguez, AM., Rodríguez, M.R., Díaz Requejo, M.M., Pérez Romero, P.J.: "Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions". Israel Journal of Chemistry. Volume 60, Issue 3-4 (2020).  https://doi.org/10.1002/ijch.201900181
NO Support for this work was provided by the MINECO (CTQ2017‐82893‐C2‐1‐R and PO FEDER 2014‐2020, UHU‐1254043). AMR and MRR thanks MEC for a FPU fellowships.
DS Repositorio Institucional de la Universidad de Huelva
RD 19 jun 2026