Heteroaromatic tosylates as electrophiles in regioselective Mizoroki-Heck-coupling reactions with electron-rich olefins.
Heteroaromatic 2-pyridyl tosylates were successfully applied as electrophiles in palladium(0)-catalyzed Mizoroki-Heck-coupling reactions to electron-rich olefins with complete alpha-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 alpha-heteroarylvinyl amides was established providing straightforward access to highly functionalized heteroaromatic compounds including chiral benzylic amide derivatives.
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus, Denmark.
Thomas M
TM
Gøgsig
Anders T
AT
Lindhardt
Mouloud
M
Dekhane
Julie
J
Grouleff
Troels
T
Skrydstrup
D000475:Alkenes / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004583:Electrons; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
D000475:Alkenes; D001593:Benzyl Compounds; D006571:Heterocyclic Compounds; D014105:Tosyl Compounds; D010165:Palladium