Synthesis Of Diversity Sulfoxide Compound

Sulfoxide compound is a very important intermediate in the fine chemicals,pharmaceuticals,pesticides,dyes,organic synthesis and a wide range of other applications.The configuration of chiral sulfoxide compound is very stable,the synthesis process is relatively easy,easy to remove the chiral induction,it can serve as a very good chiral auxiliary agents that induce occupies in the application of natural products and drugs.Our group has been working on the induction of chiral tert-butyl sulfonamide and built by a chiral tert-butyl spring chiral amide induced six-membered ring carbenes,using the chiral six-membered ring carbine to catalyzed ?,?-unsaturated ester,with very good induction effect.In this paper,the design and synthesis of a series of chiral sulfoxide compounds,discusses and studies without metal catalyst under the conditions of NBS and acid,the t-butyl of tert-butyl sulfone occurred leaving very convenient and effective to build S-C,S-N,S-O bonds.Compared with traditional methods,this method is efficient,convenient,non-metal catalysis and other advantages.The main work includes the following two aspects: First,The synthesis of chiral tert-butyl sulfone compound: We have synthesized a series of chiral tert-butyl sulfone compounds,expanding the types of chiral ter-butyl sulfoxide compounds,all compounds have been characterized by 1HNMR,13 C NMR spectroscopic,and some compounds have been characterized by chiral HPLC column,and then use the t-butyl sulfone compound to build S-C,S-N,S-O bonds.Second,To build S-C,S-N,S-O bonds with sulfoxide compounds: the traditional mothods to build S-C bonds with sulfoxide general use transition metal and a radical reaction,we use metal catalysis free,and under the condition of acid and NBS,constructed S-C bond successfully,and the method can be extended to build S-N,S-O bonds,greatly improving the usability and breadth of this method,compared with the traditional method,which is efficient,easy to use,no metal catalyst and so on.We use this method,a series of sulfoxide compounds have been synthesized,all of these compounds have been characterized by 1HNMR,13 CNMR,some of the new compounds used HR-MS spectra.