Copper-Catalyzed Carbonylative Synthesis of β-Boryl Amides via Boroamidation of Alkenes

beta-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 beta-boryl amides has been developed. Several new chemical bonds were constructed in this transformation. A wide range of beta-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.

Automated summary

The study developed a new reaction for synthesizing beta-boryl amides and successfully produced a variety of beta-boryl amides. The research also demonstrated that this method can be used for the transformation of ethylene gas, and achieved enantioselective synthesis. Additionally, the method can directly prepare anticancer drugs.