Palladium Catalyzed Direct Alkenylation of Dihydropyrrolo[2,1‐a]isoquinolines through the Oxidative Heck Reaction

Abstract

We have developed a Pd(II) catalyzed direct modification of dihydropyrrolo[2,1‐a]isoquinoline derivatives with various alkenes including acrylates, acrylamide, cyclohexenone, maleimide and styrenes. A series of highly functionalized alkenylated dihydropyrroloisoquinolines could be prepared in acceptable to good yields (up to 98 %) through oxidative Heck coupling.

Formylation and Bromination of Pyrrolo[2,1-a]isoquinoline Derivatives with Bromoisobutyrate and Dimethyl Sulfoxide

“…As the straightforward modification of complex N-containing molecules is a convenient way for the preparation of useful architectures, our laboratory have been interested in direct functionalization of a series of privileged framework-bearing molecules (Scheme ). , Recently, we have developed several direct approaches for modifying privileged N-containing frameworks such as iron-mediated dimerization of dihydropyrroloisoquinolines, iron-catalyzed cross coupling of dihydropyrroloisoquinolines with phenols, and palladium-catalyzed olefination of dihydropyrroloisoquinolines …”