Synthesis of Biphenyls via Cross-Coupling of Arenediazonium Salts

Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents: N. Riemer, C. Coswig, M. Shipman, B. Schmidt
Synlett 2018, 29, 2427–2431

Although a range of methods are available for the synthesis of functionalized biphenyls, these compounds continue to attract the attention of organic chemists owing to the versatility and usefulness of the biphenyl scaffold. The group of Professor Bernd Schmidt from the University of Potsdam (Germany) has recently reported a new Pd-catalyzed entry to biphenyl compounds using diazonium salts as substrates for cross-coupling reactions.

Professor Schmidt said: “Arenediazonium salts are still underexplored and underrated electrophilic coupling reagents in Pd-catalyzed C–C bond forming reactions. This is very surprising considering their high reactivity that allows chemists to conduct coupling reactions at ambient temperature using simple Pd pre-catalysts such as Pd(II) acetate, without any activating ligands. By combining arenediazonium salts and isolable air- and moisture stable triarylbismuth compounds we show an alternative to cross-coupling reactions with other more sensitive and sometimes ill-defined organometallic reagents for the synthesis of biaryls.”
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