Copper-catalyzed carbonylative synthesis of β-boryl amides via boroamidation of alkenes

Abstract

β-Boryl amide is a class of high value intermediates in organic chemistry. In this work, a copper-catalyzed carbonylative boroamidation of olefins toward the synthesize of β-boryl amides has been developed. Several new chemical bonds were constructed in this transformation. A wide range of β-boryl amides were produced in excellent regioselectivity and good to excellent yields. Ethylene gas can be successfully transformed under the same standard conditions as well. Notably, with the use of a chiral ligand, the first example of enantioselective carbonylative boroamidation of alkenes was realized. In addition, Piposulfan and Pipobroman, antineoplastic medicines, were prepared by this methodology in a straightforward manner.