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Rh(II)-Catalyzed Site-Selective Insertion of Quinoid Carbene into Quinoline N-Oxides to Synthesize METHOX-Inspired
Bortika Sanyal1, Subhajit Sarkar1, Kunal Chakraborty1
1Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur 721302, India.
Abstract:
A Rh(II)-catalyzed straightforward and efficient method is developed for the construction of METHOX-inspired heterobiaryls via the C2-naphtholation of quinoline N-oxide using diazonaphthoquinone as a coupling partner. In general, the reaction consists of cross-coupling between two electrophilic centers like the C2 center of quinoline N-oxide and the carbenic carbon of quinoid carbene. The developed method was extended to a scope with broad functionality. Preliminary mechanistic investigations and DFT calculations suggest a plausible reaction mechanism.
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