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Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross‐Coupling of Organolithium Reagents
Author(s) -
Heijnen Dorus,
Tosi Filippo,
Vila Carlos,
Stuart Marc C. A.,
Elsinga Philip H.,
Szymanski Wiktor,
Feringa Ben L.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700417
Subject(s) - palladium , reagent , catalysis , chemistry , aryl , alkyl , nanoparticle , combinatorial chemistry , coupling reaction , oxygen , organic chemistry , nanotechnology , materials science
The discovery of an ultrafast cross‐coupling of alkyl‐ and aryllithium reagents with a range of aryl bromides is presented. The essential role of molecular oxygen to form the active palladium catalyst was established; palladium nanoparticles that are highly active in cross‐coupling reactions with reaction times ranging from 5 s to 5 min are thus generated in situ. High selectivities were observed for a range of heterocycles and functional groups as well as for an expanded scope of organolithium reagents. The applicability of this method was showcased by the synthesis of the [ 11 C]‐labeled PET tracer celecoxib.