Copper-Catalyzed Aerobic Cross-Dehydrogenative Coupling of β-Oxime Ether Furan with Indole

Heterobiaryls serve as relevant structural motifs in many fields of high applicative importance such as drugs, agrochemicals, organic functional materials etc. Cross-dehydrogenative coupling involving direct oxidation of two C-H bonds to construct a C-C bond is actively being pursued as a more benign and 'greener' alternative for synthesizing heterobiaryls. Herein, we report a Cu(I)-catalyzed cross-dehydrogenative coupling of indoles and furans, two of the most important aromatic heterocycles using air as the terminal oxidant. The reaction proceeds with regio- and chemoselectivity to give the cross-coupled products in good to excellent yields generally. A broad substrate scope with respect to both the coupling partners has been demonstrated to prove the generality of this reaction. This represents the hitherto unexplored cross-dehydrogenative coupling methodology to obtain an indole-furan biaryl motif.

Automated summary

Heterobiaryls are important structural motifs in various fields, and the cross-dehydrogenative coupling is actively explored as a greener alternative for their synthesis. A Cu(I)-catalyzed cross-dehydrogenative coupling of indoles and furans using air as oxidant is reported here, showing high selectivity and good yields with broad substrate scope.