14011-00-8Relevant articles and documents
Heterogeneous Nickel-Catalyzed Cross-Coupling between Aryl Chlorides and Alkyllithiums Using a Polystyrene-Cross-Linking Bisphosphine Ligand
Yamazaki, Yuki,Arima, Nozomi,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 2250 - 2254 (2019/03/21)
A polystyrene-cross-linking bisphosphine ligand PS-DPPBz was used for Ni-catalyzed cross-coupling with organolithiums. A bench-stable precatalyst [NiCl2(PS-DPPBz)] enabled efficient coupling reactions between aryl chlorides and alkyllithiums. The heterogeneous Ni system showed good reusability. (Figure presented.).
Effect of solvent on the lithium-bromine exchange of aryl bromides: Reactions of n-butyllithium and tert-butyllithium with 1-bromo-4-tert- butylbenzene at 0 °C
Bailey, William F.,Luderer, Mark R.,Jordan, Kevin P.
, p. 2825 - 2828 (2007/10/03)
The outcome of reactions of 1-bromo-4-tert-butylbenzene (1), a representative aryl bromide, with n-BuLi or t-BuLi at 0 °C in a variety of solvent systems has been investigated. The products of reactions of 1 with n-BuLi vary significantly with changes in solvent composition: 1 does not react with n-BuLi in pure heptane; the exchange reaction to give (4-tert-butylphenyl) lithium, which is slow in pure diethyl ether, is virtually quantitative in heptane containing a small quantity of THF; and the reaction of 1 with n-BuLi in THF leads to considerable coupling. Lithium-bromine exchange is the virtually exclusive outcome of reactions of 1 with t-BuLi in every solvent studied except pure heptane: the presence of a small quantity of any of a variety of structurally diverse ethers (Et2O, THF, THP, MTBE) in the predominantly hydrocarbon medium affords (4-tert-butylphenyl)lithium, assayed as tert-butylbenzene, in yields exceeding 97%. The only side products observed from reactions of 1 with t-BuLi are small amounts of benzyne-derived hydrocarbons.
Tetraphosphine/palladium catalysed Suzuki cross-coupling reactions of aryl halides with alkylboronic acids
Kondolff, Isabelle,Doucet, Henri,Santelli, Maurice
, p. 3813 - 3818 (2007/10/03)
Through the use of [PdCl(C3H5)]2/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as a catalyst, a range of aryl bromides and chlorides undergoes Suzuki cross-coupling with alkylboronic acids in good yields. Several alkyl substituents such as ethyl, n-butyl, n-octyl, isobutyl or 2,2-dimethylpropyl on the alkylboronic acids have been successfully used. The functional group tolerance on the aryl halide is remarkable; substituents such as fluoro, methyl, methoxy, acetyl, formyl, benzoyl, nitro or nitrile are tolerated. Furthermore, this catalyst can be used at low loading, even for reactions of sterically hindered aryl bromides.