Green Chemical Synthesis of 2-Benzenesulfonyl-pyridine and Related Derivatives
摘要:
A practical synthesis of 2-benzenesulfonylpyridine, 1, is described which is a key starting material for the manufacture of an investigational new drug candidate at Eli Lilly and Company. An optimized green chemical process was developed which features a novel tandem SNAr/oxidation under mild conditions to produce the target sulfone, 1, in 86% yield and >99% purity. In addition, this novel, environmentally friendly methodology was found to be general for the synthesis of substituted aromatic pyridyl sulfides and sulfones.
Copper-catalyzeddecarboxylative thiolation using molecular oxygen as the sole oxidant was developed. A variety of aromaticcarboxylicacids including 2-nitrobenzoic acids, pentafluorobenzoic acid and several heteroaromatic carboxylicacids undergo efficient...
A simple approach for copper-promoted S-arylation reactions utilizing triarylbismuths or triarylantimonys as arylating reagents has been described. These reactions can be performed under mild conditions and exhibit remarkable functional group tolerance and chemoselectivity. The corresponding 2-arylthiopyridine 1-oxide derivatives and arylthioanilines/phenols have been successfully synthesized, achieving