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

Wen-Bo Shen, Qing Sun, Long Li, Xin Liu, Bo Zhou, Juan-Zhu Yan, Xin Lu () and Long-Wu Ye ()
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Wen-Bo Shen: College of Chemistry and Chemical Engineering, Xiamen University
Qing Sun: Xiamen University
Long Li: College of Chemistry and Chemical Engineering, Xiamen University
Xin Liu: College of Chemistry and Chemical Engineering, Xiamen University
Bo Zhou: College of Chemistry and Chemical Engineering, Xiamen University
Juan-Zhu Yan: College of Chemistry and Chemical Engineering, Xiamen University
Xin Lu: Xiamen University
Long-Wu Ye: College of Chemistry and Chemical Engineering, Xiamen University

Nature Communications, 2017, vol. 8, issue 1, 1-9

Abstract: 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 in generating α-oxo gold carbenes. Among those, gold-catalyzed oxidative cyclization of dialkynes has received particular attention as this chemistry offers great potential to build structurally complex cyclic molecules. However, these alkyne oxidations have been mostly limited to noble metal catalysts, and, to our knowledge, non-noble metal-catalyzed reactions such as diyne oxidations have not been reported. Herein, we disclose a copper-catalyzed oxidative diyne cyclization, allowing the facile synthesis of a wide range of valuable pyrrolo[3,4-c]quinolin-1-ones. Interestingly, by employing the same starting materials, the gold-catalyzed cascade cyclization leads to the divergent formation of synthetically useful pyrrolo[2,3-b]indoles. Furthermore, the proposed mechanistic rationale for these cascade reactions is strongly supported by both control experiments and theoretical calculations.

Date: 2017
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DOI: 10.1038/s41467-017-01853-1

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