Selective Synthesis of Alkynylated Isoquinolines and Biisoquinolines via RhIII Catalyzed C–H Activation/1,3-Diyne Strategy

Described herein is a convenient and highly selective synthesis of alkynylated isoquinolines and biisoquinolines from various aryl ketone O-pivaloyloxime derivatives and 1,3-diynes via rhodium-catalyzed C–H bond activation. In this transformations, alkynylated isoquinolines, 3,4′- and 3,3′-biisoquinolines could be obtained respectively through changing the reaction conditions. Mechanistic investigation revealed that the C–H activation of aryl ketone O-pivaloyloxime was the key step to this reaction.本文报道了一种便捷且高选择性的合成方法：以多种芳基酮O-新戊酰肟衍生物与1,3-二炔为起始原料，通过铑催化C–H键活化策略，制备炔基化异喹啉与联异喹啉类化合物。通过调整反应条件，可分别得到炔基化异喹啉、3,4'-联异喹啉以及3,3'-联异喹啉。机理研究表明，芳基酮O-新戊酰肟的C–H键活化是该反应的关键步骤。