7552-55-8Relevant articles and documents
Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates
Smedley, Christopher J.,Barrow, Andrew S.,Spiteri, Christian,Giel, Marie-Claire,Sharma, Pallavi,Moses, John E.
, p. 9990 - 9995 (2017/08/01)
Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.
Process for the preparation of fluorinated benzene sulfonyl fluorides
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, (2008/06/13)
The present invention relates to a process for the preparation of a fluorinated benzene sulfonyl fluoride comprising the step of: heating a benzene sulfonyl fluoride of the Formula (I) STR1 where Y is fluorine, chlorine, bromine, iodine, a methyl group, an ethyl group, or a propyl group; p is 0 to 3; and q is 2 to 6, in the presence of an alkali metal fluoride under conditions and for a time sufficient to provide a fluorinated benzene sulfonyl fluoride of the Formula (II) STR2 where x is 1 to 5; m=q-x; and Y and p are as defined above. The present invention also provides novel benzene sulfonyl fluorides of the Formula (III) STR3 where each Y is meta or para to --SO2 F and is independently selected from the group consisting of chlorine, fluorine, fluorosulfonyl, methyl group, ethyl group, and propyl group; and p is 1 or 2. The fluorinated benzene sulfonyl fluorides are versatile fluorinated intermediates. They are readily converted to sulfonamides of potential activity, or the sulfonyl group can be converted into another functional group, or removed to provide fluorinated benzenes.