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Pyrrole Functionalization by Copper‐Catalyzed Nitrene Transfer Reactions
Author(s) -
Rodríguez Anabel M.,
Rodríguez Manuel R.,
DíazRequejo M. Mar,
Pérez Pedro J.
Publication year - 2020
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201900181
Subject(s) - chemistry , nitrene , pyrrole , catalysis , medicinal chemistry , imine , surface modification , nucleophile , amination , polymer chemistry , photochemistry , combinatorial chemistry , stereochemistry , organic chemistry
The catalytic functionalization of pyrroles by incorporation of a nitrene group is reported. The C α ‐H bond of 1H‐pyrrole is amidated upon the formal insertion of the NTs (Ts=p‐toluenesulfonyl) group catalyzed by Tp Br3 Cu(NCMe) (Tp Br3 =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.