Catalytic Azoarene Synthesis from Aryl Azides Enabled by a Dinuclear Ni Complex

Journal of the American Chemical Society
Ian G PowersChristopher Uyeda

Abstract

Azoarenes are valuable chromophores that have been extensively incorporated as photoswitchable elements in molecular machines and biologically active compounds. Here, we report a catalytic nitrene dimerization reaction that provides access to structurally and electronically diverse azoarenes. The reaction utilizes aryl azides as nitrene precursors and generates only gaseous N2 as a byproduct. By circumventing the use of a stoichiometric redox reagent, a broad range of organic functional groups are tolerated, and common byproducts of current methods are avoided. A catalyst featuring a Ni-Ni bond is found to be uniquely effective relative to those containing only a single Ni center. The mechanistic origins of this nuclearity effect are described.

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Citations

Sep 6, 2018·Chemistry : a European Journal·Takuya ShimbayashiKouichi Ohe
Feb 13, 2019·Chemistry : a European Journal·Tobias W MorrisSteven L Tait
Jun 28, 2019·Chemical Communications : Chem Comm·Shi-Ming ChenSong Gao
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