CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization to access 5,6-dihydro-pyrrolo[2,1-a]isoquinolines

Org Biomol Chem. 2020 Sep 21;18(35):6889-6898. doi: 10.1039/d0ob01403f. Epub 2020 Aug 27.

Abstract

An efficient and enviromentally friendly CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization cascade was realized with N-substituted tetrahydroisoquinolines and electron-deficient olefins. Under the mild conditions, the reaction proceeded smoothly and displayed excellent functional group tolerance, affording 5,6-dihydro-pyrrolo[2,1-a]isoquinolines in good to high yields. This protocol exhibits a broad substrate scope to both N-alkyl tetrahydroisoquinolines and dipolarophile substrates.

Publication types

  • Research Support, Non-U.S. Gov't