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

Publisher: John Wiley & Sons Inc

E-ISSN: 1099-0690|2015|34|7519-7528

ISSN: 1434-193x

Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, Vol.2015, Iss.34, 2015-12, pp. : 7519-7528

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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.