An Interrupted Pummerer/Nickel‐Catalysed Cross‐Coupling Sequence |
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| Authors: | Miles H. Aukland Fabien J. T. Talbot Dr. José A. Fernández‐Salas Dr. Matthew Ball Dr. Alexander P. Pulis Prof. Dr. David J. Procter |
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| Affiliation: | 1. School of Chemistry, University of Manchester, Manchester, UK;2. Pharmaceutical Technology and Development, AstraZeneca, Macclesfield, UK |
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| Abstract: | 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. |
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| Keywords: | cross-coupling nickel catalysis Pummerer reactions sulfonium salts sulfoxides |
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