Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki–Heck‐Coupling Reactions with Electron‐Rich Olefins

• Published in: Chemistry : a European journal Vol. 15; no. 24; pp. 5950 - 5955
• Main Authors: Gøgsig, Thomas M., Lindhardt, Anders T., Dekhane, Mouloud, Grouleff, Julie, Skrydstrup, Troels
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 08.06.2009; Wiley
• Subjects: Alkenes - chemistry; aryl tosylates; Benzyl Compounds - chemical synthesis; Benzyl Compounds - chemistry; Chemistry; Chemistry, Multidisciplinary; CC coupling; Electrons; heterocycles; Heterocyclic Compounds - chemical synthesis; Heterocyclic Compounds - chemistry; Mizoroki–Heck coupling; Molecular Structure; palladium; Palladium - chemistry; Physical Sciences; Science & Technology; Stereoisomerism; Tosyl Compounds - chemistry; C-C coupling; CONVENIENT SYNTHESIS; SUZUKI; Mizoroki-Heck coupling; HYDROXYALKYL VINYL ETHERS; BROMIDES; ARYLBORONIC ACIDS; MILD CONDITIONS; heterocycles; ARYL HALIDES; PALLADIUM-CATALYZED ARYLATION; CHLORIDES; palladium; ASYMMETRIC HYDROGENATION; aryl tosylates
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.200900313

Easy and direct: Regioselective Mizoroki–Heck‐coupling reactions using heteroaromatic tosylates as electrophiles were achieved, thus providing direct and easy access to highly functionalized α‐heteroarylvinyl amides and ethers. Heteroaromatic 2‐pyridyl tosylates were successfully applied as electrophiles in palladium(0)‐catalyzed Mizoroki–Heck‐coupling reactions to electron‐rich olefins with complete α‐regioselectivity. This protocol represents a general strategy for the application of pyridyl tosylates and mesylates in the Mizoroki–Heck coupling. The catalytic system also proved adaptable to changes in the heteroaromatic core as well as large‐scale applications. Finally, the synthetic utility of the functionalized α‐heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives. Easy and direct: Regioselective Mizoroki–Heck‐coupling reactions using heteroaromatic tosylates as electrophiles were achieved, thus providing direct and easy access to highly functionalized α‐heteroarylvinyl amides and ethers.