Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 11, Pages 4110-4118Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b00503
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Funding
- NSF [CHE-1554787, CHE-1625543, DGE-1333468]
- Purdue University
- National Science Foundation [ACI-1548562, TG-CHE150051]
- Division Of Chemistry [1625543] Funding Source: National Science Foundation
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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 N-2 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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