Divergent synthesis of N-heterocycles via controllable cyclization of azido-diynes catalyzed by copper and gold

• DOI: 10.1038/s41467-017-01853-1
• Publication Date: 2017-11-17T23:33:20Z
• Authors: Wen-Bo Shen; Qing Sun; Long Li; Xin Liu; Bo Zhou; Juan-Zhu Yan; Xin Lu; Long-Wu Ye
• Keywords: Alkyne; Noble metal

Abstract Gold-catalyzed intermolecular alkyne oxidation by an N–O bond oxidant has proven to be a powerful method in organic synthesis during the past decade, because this approach would enable readily available alkynes as precursors generating α-oxo gold carbenes. Among those, gold-catalyzed oxidative cyclization of dialkynes received particular attention chemistry offers great potential build structurally complex cyclic molecules. However, these oxidations have been mostly limited noble metal catalysts, and, our knowledge, non-noble metal-catalyzed reactions such diyne not reported. Herein, we disclose copper-catalyzed cyclization, allowing facile wide range valuable pyrrolo[3,4- c ]quinolin-1-ones. Interestingly, employing same starting materials, cascade leads divergent formation synthetically useful pyrrolo[2,3- b ]indoles. Furthermore, proposed mechanistic rationale for is strongly supported both control experiments and theoretical calculations.