Kumada Coupling of Aryl and Vinyl Tosylates under Mild Conditions

• Published in: Journal of organic chemistry Vol. 70; no. 23; pp. 9364 - 9370
• Main Authors: Limmert, Michael E, Roy, Amy H, Hartwig, John F
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 11.11.2005; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Exact sciences and technology; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Palladium - pharmacology; Physical Sciences; Preparations and properties; Science & Technology; Tosyl Compounds - chemistry; PALLADIUM; EFFICIENT CATALYST; SULFONATES; ARENESULFONATES; MESYLATES; CHLORIDES; AMIDATION; SECONDARY ALKYL-HALIDES; BROMIDES; GRIGNARD-REAGENTS; Catalytic reaction; Transition element complexes; Mild operating conditions; Palladium complex; Transition metal; Transition metal Complexes; Grignard reagent; Vinylic compound; Platinoid Complexes; Aromatic compound; Chemical reactivity; Chemical synthesis; Ethylenic compound
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo051394l

Aryl and alkenyl tosylates are easily prepared, inexpensive and, thus, attractive for transition-metal-catalyzed couplings, but their reactivity is low. We report examples of mild, palladium-catalyzed coupling of aryl, alkenyl, and alkyl Grignard reagents with aryl and alkenyl tosylates. The resulting biaryls, vinylarenes, and alkylarenes were isolated in good to excellent yield. These couplings were conducted with a nearly equimolar ratio of the two reactants, and many examples were conducted at room temperature.