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Nickel‐Catalyzed Cross‐Coupling of Organolithium Reagents with (Hetero)Aryl Electrophiles
Author(s) -
Heijnen Dorus,
Gualtierotti JeanBaptiste,
Hornillos Valentín,
Feringa Ben L.
Publication year - 2016
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.201505106
Subject(s) - electrophile , nickel , reagent , aryl , chemistry , catalysis , carbene , halogen , combinatorial chemistry , metal , organic chemistry , coupling reaction , polymer chemistry , alkyl
Nickel‐catalyzed selective cross‐coupling of aromatic electrophiles (bromides, chlorides, fluorides and methyl ethers) with organolithium reagents is presented. The use of a commercially available nickel N ‐heterocyclic carbene (NHC) complex allows the reaction with a variety of (hetero)aryllithium compounds, including those prepared via metal‐halogen exchange or direct metallation, whereas a commercially available electron‐rich nickel‐bisphosphine complex smoothly converts alkyllithium species into the corresponding coupled product. These reactions proceed rapidly (1 h) under mild conditions (room temperature) while avoiding the undesired formation of reduced or homocoupled products.