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Gold(III)‐Catalyzed Site‐Selective and Divergent Synthesis of 2‐Aminopyrroles and Quinoline‐Based Polyazaheterocycles
Author(s) -
Zeng Zhongyi,
Jin Hongming,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2018
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.201810369
Subject(s) - quinoline , annulation , catalysis , moiety , combinatorial chemistry , chemistry , nucleophile , carbene , tandem , substrate (aquarium) , quenching (fluorescence) , nucleophilic addition , cascade reaction , stereochemistry , organic chemistry , materials science , oceanography , physics , quantum mechanics , composite material , fluorescence , geology
Abstract A facile, site‐selective, and divergent approach to construct 2‐aminopyrroles and quinoline‐fused polyazaheterocycles enabled by a simple gold(III) catalyst from ynamides and anthranils under mild reaction conditions is described. This one‐pot strategy uses readily available starting materials, proceeds in a highly step‐ and atom‐economical manner, with broad substrate scope and scale‐up potential. The key element for success in this tandem reaction is a catalyst‐directed preferred quenching of the in situ generated gold carbene intermediates by a nucleophilic benzyl/2‐furylmethyl moiety on the ynamides as an alternative to the known C−H annulation leading to indoles.