1-Bromo-4-(S-methylsulfonimidoyl)benzene (BD336512) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 4381-25-3 and 83730-53-4.
At ambient temperature, deprotonated sulfoximines R1S(O)(R2)=NH (R1 = Ph, 2-naphthyl, 2-pyridyl, 2-thienyl, etc.; R2 = Me, phenyl) react with 1-trifluoromethylalkenes ArC=CH2(CF3) (Ar = Ph, 1-naphthyl, 2-benzofuryl, 3-pyridyl, etc.) to provide either N- or C-gem-difluoroalkenylated products R1S(O)(R2)=NCH2C(Ar)=CF2. The reaction site depends upon the N substituent of the starting material. The optimal conditions involve the use of a superbasic system NaOH in DMSO. The reactions are characterized by a broad substrate scope and medium to high yields. Scale-up experiments of both the N- and C-gem-difluoroalkenylations proceeded well. Treatment of N-difluoroallyl sulfoximine with 4-methoxybenzene-1-thiol under dioxygen afforded the corresponding oxygenated addition product {3,3-difluoro-2-hydroxy-3-[(4-methoxyphenyl)thio]-2-phenylpropyl}imino(methyl)(phenyl)l6-sulfanone.
Superbase-Mediated gem-Difluoroalkenylations of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2
Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem