Ab road-spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of acatalytic amount of 1-hydroxybenzotriazole(HOBt) and silicon additives,amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87-99 %). Noticeably,t his protocol is particularly efficient for sterically hindered substrates.Catalyst loading is generally low and only 0.02 mol %o fc atalyst is required for the multidecagram-scale synthesis of an amantadine derivative.Inaddition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via ak ey intermediate sulfonyl fluoride 13.S ince al arge number of amines are commercially available,t his route provides af acile entry to access Fedratinib analogues for biological screening.
Annulations of ortho-phosphinoarenesulfonyl fluorides
with trimethylsilyl azide were developed to access an unprecedented
benzo-1,2,3-thiazaphosphole heterocycle. A corresponding reaction
mechanism was proposed and further elucidated by experimental and
computational studies. The reaction proceeds through a Staudinger-type
iminophosphorane intermediate followed by intramolecular trapping
with sulfonyl fluoride.
A series of air-stable, easily accessible tridentate ferrocene-based diamine-phosphine sulfonamide (f-diaphos) ligands were successfully developed for iridium-catalyzed asymmetric hydrogenation of ketones. The f-diaphos ligands exhibited excellent enantioselectivity and superb reactivity in Ir-catalyzed asymmetric hydrogenation of ketones (for arylalkyl ketones, ( S)-selectivity, up to 99.4% ee, and 100 000 TON; for diaryl ketones, ( R)-selectivity, up to 98.2% ee, and 10 000 TON). This protocol could be easily conducted on gram scale, thereby providing a chance to various drugs.
Regional and stereoselective construction of spirooxindole-fused spiropyrazolones containing contiguous three stereogenic centres via [3 + 2] annulation catalyzed by ferrocene derived bifunctional phosphine.
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