An Interrupted Pummerer/Nickel-Catalysed Cross-Coupling Sequence.
Miles H AuklandFabien J T TalbotJosé A Fernández-SalasMatthew BallAlexander P PulisDavid J ProcterPublished in: Angewandte Chemie (International ed. in English) (2018)
An interrupted Pummerer/nickel-catalysed cross-coupling strategy has been developed and used in the elaboration of styrenes. The operationally simple method can be carried out as a one-pot process, involves the direct formation of stable alkenyl sulfonium salt intermediates, utilises a commercially available sulfoxide, catalyst, and ligand, operates at ambient temperature, accommodates sp-, sp2 -, and sp3 -hybridised organozinc coupling partners, and delivers functionalised styrene products in high yields over two steps. An interrupted Pummerer/cyclisation approach has also been used to access carbo- and heterocyclic alkenyl sulfonium salts for cross-coupling.