A concise and efficient one-pot synthesis of functionalized sulfonylated pyridines via an S(N)Ar reaction of readily available pyridines and sodium sulfinate salts in the presence of tetrabutylammonium chloride is presented.
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A Practical, One-Pot Synthesis of Sulfonylated Pyridines. -Electron-deficient chloro-, bromo-, iodo-pyridines or a triflate (XIV) are sulfonylated using Bu4NCl as a catalyst in DMA. Electron-neutral or electron-rich chloropyridines require HCl in addition to achieve good results. The reaction can be scaled-up. Chloropyrazine is sulfonylated easily; in the case of chloroquinoline (XVIII), it is crucial to avoid any traces of water to prevent hydrolysis. Dichloropyridine (XX) undergoes bissulfonylation, whereas the second chlorine in (Ie), (VId) and (XXII) remains unchanged. -(MALONEY*, K. M.; KUETHE, J. T.; LINN, K.; Org. Lett. 13 (2011) 1, 102-105, http://dx.
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