Oxygen Activated, Palladium Nanoparticle Catalyzed, Ultrafast Cross‐Coupling of Organolithium Reagents | Zendy

Heijnen Dorus | Zendy; Tosi Filippo | Zendy; Vila Carlos | Zendy; Stuart Marc C. A. | Zendy; Elsinga Philip H. | Zendy; Szymanski Wiktor | Zendy; Feringa Ben L. | Zendy

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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.

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