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Palladium‐Catalyzed Direct CH Alkylation of Electron‐Deficient Pyrrole Derivatives
Author(s) -
Jiao Lei,
Bach Thorsten
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201301154
Subject(s) - alkylation , pyrrole , chemistry , catalysis , palladium , medicinal chemistry , yield (engineering) , norbornene , organic chemistry , materials science , copolymer , polymer , metallurgy
The apparent and the real : What looks like a Friedel–Crafts alkylation reaction of electron‐deficient pyrroles is actually a Pd II ‐catalyzed, norbornene‐mediated CH activation reaction, in which the alkylation of the pyrrole core occurs by reductive elimination. As well as ethyl‐1 H ‐pyrrole‐2‐carboxylate (see scheme), several other 2,3‐disubstituted pyrroles underwent the selective C5 alkylation in good yield.