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Synthesis of ( Z )‐ N ‐Alkenylazoles and Pyrroloisoquinolines from α‐ N ‐Azoleketones through Pd‐Catalyzed Tosylhydrazone Cross‐Couplings
Author(s) -
Florentino Lucía,
Aznar Fernando,
Valdés Carlos
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201301057
Subject(s) - catalysis , tandem , aryl , intramolecular force , alkene , chemistry , combinatorial chemistry , stereoselectivity , stereochemistry , halide , computer science , medicinal chemistry , database , organic chemistry , materials science , alkyl , composite material
Azoles reacting in tandem : The ortho ‐stereodirecting effect is the key to the stereoselective synthesis of ( Z )‐ N ‐alkenylazoles I through the tosylhydrazide‐mediated Pd‐catalyzed cross‐coupling reaction of α‐ N ‐azoleacetophenones with ortho ‐substituted aryl halides and nonaflates (see scheme). Additionally, the preorganization of the alkene allowed for the development of an auto‐tandem reaction involving an intramolecular CH arylation leading to pyrroloisoquinolines II .