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Pd(0)‐Catalyzed Cu(I)‐Thiophene‐2‐carboxylate‐mediated Cross‐Coupling of Heteroaromatic Thioethers and Boronic Acids—First Liebeskind–Srogl Reaction in Water
Author(s) -
Koley Moumita,
Wimmer Laurin,
Schnürch Michael,
Mihovilovic Marko D.
Publication year - 2013
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2005
Subject(s) - chemistry , catalysis , pyridine , benzothiazole , coupling reaction , thiophene , carboxylate , boronic acid , aqueous solution , organic chemistry , solvent , aqueous medium , copper , medicinal chemistry , polymer chemistry
The first example of a Liebeskind–Srogl cross‐coupling reaction in water as sole reaction solvent is reported. 2‐(Methylthio)pyridine and 2‐(methylthio)benzothiazole were reacted in the presence of a Pd(0) catalyst and copper(I) thiophene‐2‐carboxylate with a series of arylboronic acids. These cross coupling reactions in water proceeded well with electron‐rich boronic acids and gave comparable yields to literature examples using organic solvents. Electron‐poor boronic acids gave somewhat lower yields in aqueous medium.