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Heteroaromatic Tosylates as Electrophiles in Regioselective Mizoroki–Heck‐Coupling Reactions with Electron‐Rich Olefins
Author(s) -
Gøgsig Thomas M.,
Lindhardt Anders T.,
Dekhane Mouloud,
Grouleff Julie,
Skrydstrup Troels
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900313
Subject(s) - regioselectivity , electrophile , chemistry , amide , combinatorial chemistry , catalysis , heck reaction , organic chemistry , palladium
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.