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Stable Cyclic (Alkyl)(Amino)Carbenes as Rigid or Flexible, Bulky, Electron‐Rich Ligands for Transition‐Metal Catalysts: A Quaternary Carbon Atom Makes the Difference
Author(s) -
Lavallo Vincent,
Canac Yves,
Präsang Carsten,
Donnadieu Bruno,
Bertrand Guy
Publication year - 2005
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.200501841
Subject(s) - steric effects , alkyl , catalysis , chemistry , aryl , transition metal , carbon atom , palladium , quaternary carbon , atom (system on chip) , carbon fibers , metal , medicinal chemistry , combinatorial chemistry , organic chemistry , materials science , enantioselective synthesis , composite number , computer science , composite material , embedded system
Like NHCs? Not quite : Cyclic (alkyl)(amino)carbenes (CAACs) are strong σ‐donors and have steric environments that differ dramatically from those of bulky, electron‐rich phosphines ( A ) and cyclic diaminocarbenes ( B ). These readily available carbenes are desirable ligands for catalysis, as illustrated by the first palladium‐mediated α‐arylation of ketones and aldehydes with non‐activated aryl chlorides at ambient temperature.