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An Interrupted Pummerer/Nickel‐Catalysed Cross‐Coupling Sequence
Author(s) -
Aukland Miles H.,
Talbot Fabien J. T.,
FernándezSalas José A.,
Ball Matthew,
Pulis Alexander P.,
Procter David J.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805396
Subject(s) - sulfonium , pummerer rearrangement , sulfoxide , chemistry , nickel , catalysis , ligand (biochemistry) , combinatorial chemistry , coupling (piping) , salt (chemistry) , polymer chemistry , organic chemistry , materials science , acetic anhydride , biochemistry , receptor , metallurgy
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‐, sp 2 ‐, and sp 3 ‐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.