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Desulfitative Carbon–Carbon Cross‐Coupling of Thioamide Fragments with Boronic Acids
Author(s) -
Prokopcová Hana,
Kappe C. Oliver
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600566
Subject(s) - chemistry , thioamide , sulfur , carbon fibers , copper , palladium , catalysis , stoichiometry , coupling reaction , inorganic chemistry , organic chemistry , materials science , composite number , composite material
A novel and general carbon–carbon cross‐coupling reaction between cyclic thioamides and boronic acids is described. The reaction is catalytic in palladium(0) and requires stoichiometric amounts of a copper( I ) carboxylate as metal cofactor. The mode of cross‐coupling in the reaction of cyclic thioamides with boronic acids is easily tunable between carbon–carbon and carbon–sulfur cross‐coupling. While the catalytic palladium(0)/copper( I ) system provides carbon–carbon bond formation with extrusion of sulfur, stoichiometric quantities of copper( II ) under air mediate carbon–sulfur bond formation.