Direct Vinylation and Difluorovinylation of Arylboronic Acids Using Vinyl- and 2,2-Difluorovinyl Tosylates via the Suzuki−Miyaura Cross Coupling

• Published in: Journal of organic chemistry Vol. 73; no. 9; pp. 3404 - 3410
• Main Authors: Gøgsig, Thomas M, Søbjerg, Lina S, Lindhardt, Anders T, Jensen, Kim L, Skrydstrup, Troels
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.05.2008; Amer Chemical Soc
• Subjects: Boronic Acids - chemistry; Chemistry; Chemistry, Organic; Cross-Linking Reagents - chemistry; Electrons; Exact sciences and technology; Fluorine Compounds - chemical synthesis; Fluorine Compounds - chemistry; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Styrene - chemistry; Tosyl Compounds - chemistry; Vinyl Compounds - chemical synthesis; Vinyl Compounds - chemistry; ARENESULFONATES; POTASSIUM VINYLTRIFLUOROBORATE; ARYL HALIDES; PHOSPHATES; ILLUSTRATION; ORGANOSILICON REAGENTS; PALLADIUM CATALYST; ALKENYL BROMIDES; HECK REACTION; METATHESIS; Catalytic reaction; Palladium complex; Organic halogen compounds; Vinylation; Chemical coupling; Suzuki coupling; Styrene derivatives; Vinylic compound; Cross reaction; Boron Organic compounds; Aromatic compound; Boronic acids; Electrophile
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo7027097

General reaction conditions were developed for the Pd(0)-catalyzed Suzuki−Miyaura coupling reaction of aryl boronic acids with a simple electrophilic vinylation reagent, vinyl tosylate, providing access to styrene derivatives in good yields. The easily accessible vinyl tosylate represents a stable and less toxic alternative to the vinyl halides and the triflate/nonaflate derivatives. Furthermore, this methodology was expanded to provide a facile and straightforward approach for the introduction of a gem-difluorovinyl substituent onto an aromatic ring using the similar and also readily available 2,2-difluorovinyl tosylate as the electrophilic complement.