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The Influence of the Quinoline Moiety on Direct Pd‐Catalyzed Arylation of Five‐Membered Heterocycles
Author(s) -
Štefane Bogdan,
Grošelj Uroš,
Svete Jurij,
Požgan Franc,
Kočar Drago,
Brodnik Žugelj Helena
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800842
Subject(s) - chemistry , regioselectivity , furan , thiophene , moiety , quinoline , pyrrole , deprotonation , metalation , electrophile , reactivity (psychology) , palladium , electrophilic substitution , medicinal chemistry , negishi coupling , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , medicine , ion , alternative medicine , pathology
Herein we report a study on the reactivity of C2‐quinoline‐substituted furan, thiophene and pyrrole derivatives in palladium‐catalyzed direct C–H arylation. The regioselectivity of the reaction was strongly influenced by site position of the attached five‐membered heterocycle thus giving rise to C3‐ and/or C5‐arylated products. Furthermore, the Hammett correlation performed on 5‐substituted‐8‐(furan‐2‐yl)quinolines indicates that a marginally positive charge is building up in the rate determining transition state and thus pointing towards the electrophilic metalation‐deprotonation reaction mechanism.