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Triarylbismuthanes as Threefold Aryl‐Transfer Reagents in Regioselective Cross‐Coupling Reactions with Bromopyridines and Quinolines
Author(s) -
Rao Maddali L. N.,
Dhanorkar Ritesh J.
Publication year - 2014
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.201402455
Subject(s) - chemistry , reagent , regioselectivity , aryl , combinatorial chemistry , reactivity (psychology) , coupling (piping) , coupling reaction , organic chemistry , catalysis , alkyl , medicine , mechanical engineering , alternative medicine , pathology , engineering
Cross‐coupling studies using bromopyridines and bromoquinolines with triarylbismuths as threefold coupling reagents in substoichiometric amounts under Pd‐catalysed conditions are disclosed. The reactivity was high with both mono‐ and dibromopyridyl substrates, and mono‐ and bis‐couplings were carried out regioselectively. A library of monoaryl and diaryl pyridines was formed in high yields. A one‐pot strategy provided a simple and straightforward synthesis of both symmetrical and unsymmetrical diarylpyridines. Arylations of 2‐bromo‐ and 3‐bromoquinolines were achieved with triarylbismuth reagents. This study demonstrates that triarylbismuths may be used as threefold arylating reagents for the synthesis of aryl pyridines and quinolines through couplings with bromopyridines and bromoquinolines under Pd‐catalysed conditions.