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2,2?-Homocoupled Azine N,N?-Dioxides or Azine N-Oxides: CDC- or SNAr-Controlled Chemoselectivity
An unprecedented Cu(OAc)2- and LiOtBu-mediated homocoupling of azine N-oxides to yield 2,2?-azine N,N?-dioxides is reported. This is the first instance in which copper has been used to catalyze the homodimerization reaction, especially of 2-phenylpyridine N-oxides. In the absence of catalytic copper, the reaction follows an alternative pathway, and instead of dioxides it yields 2,2?-azine N-monoxides. This latter protocol works efficiently with a range of N-heterocyclic oxides of pyridine, 2-phenylpyridine, quinoline and N-aryl-1,2,3-triazole. It is scalable, offers high regioselectivity and gives the products in moderate to high yields. The observed chemoselectivity between the copper-assisted and copper-free protocols is routed through oxidative cross-dehydrogenative coupling (CDC) and nucleophilic aromatic substitution of hydrogen (SNAr) pathways, respectively.
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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem