European Journal of Organic Chemistry · 2014 · 37 citations · 106 references
Natural SciencesChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryCross-coupling ReactionsHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisPyridine SynthesisQuinoline ChemistryQuinoline SynthesisRegioselective Catalysis
Abstract 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.
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Kelvin L. Billingsley, Stephen L. Buchwald · Journal of the American Chemical Society · 2007 · 570 citations
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