RhIII‐Catalyzed Dehydrogenative Coupling of Quinoline N‐Oxides with Alkenes: N‐Oxide as Traceless Directing Group for Remote C–H Activation

Abstract

AbstractA RhIII‐catalyzed dehydrogenative coupling reaction of quinoline N‐oxides with alkenes has been developed that provides C‐8 olefinated quinoline derivatives by employing a remote C–H activation strategy. Main features of this catalytic method include the use of N‐oxide as a traceless directing group, the high selectivity of the reaction for the C‐8 position, and the broad scope of possible substrates. Mechanistic studies have also been performed. A five‐membered rhodacycle of quinoline N‐oxide, a possible key reaction intermediate, was synthesized and characterized for the first time.