58632-85-2Relevant academic research and scientific papers
Scalable Negishi Coupling between Organozinc Compounds and (Hetero)Aryl Bromides under Aerobic Conditions when using Bulk Water or Deep Eutectic Solvents with no Additional Ligands
Dilauro, Giuseppe,Azzollini, Claudia S.,Vitale, Paola,Salomone, Antonio,Perna, Filippo M.,Capriati, Vito
supporting information, p. 10632 - 10636 (2021/04/09)
Pd-catalyzed Negishi cross-coupling reactions between organozinc compounds and (hetero)aryl bromides have been reported when using bulk water as the reaction medium in the presence of NaCl or the biodegradable choline chloride/urea eutectic mixture. Both C(sp3)-C(sp2) and C(sp2)-C(sp2) couplings have been found to proceed smoothly, with high chemoselectivity, under mild conditions (room temperature or 60 °C) in air, and in competition with protonolysis. Additional benefits include very short reaction times (20 s), good to excellent yields (up to 98 %), wide substrate scope, and the tolerance of a variety of functional groups. The proposed novel protocol is scalable, and the practicability of the method is further highlighted by an easy recycling of both the catalyst and the eutectic mixture or water.
Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides
Sumida, Yuto,Sumida, Tomoe,Hosoya, Takamitsu
, p. 3590 - 3601 (2017/08/16)
A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o -borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.
Cobalt-catalyzed ortho alkylation of aromatic imines with primary and secondary alkyl halides
Gao, Ke,Yoshikai, Naohiko
supporting information, p. 9279 - 9282 (2013/07/19)
We report here cobalt-N-heterocyclic carbene catalytic systems for the ortho alkylation of aromatic imines with alkyl chlorides and bromides, which allows the introduction of a variety of primary and secondary alkyl groups at room temperature. The stereochemical outcomes of the reaction of secondary alkyl halides suggest that the present reaction involves single-electron transfer from a cobalt species to the alkyl halide to generate the corresponding alkyl radical. A cycloalkylated product obtained by this method can be transformed into unique spirocycles through manipulation of the directing and cycloalkyl groups.
Unexpected cross-coupling reaction between o-chloroaryl ketones and organomanganese reagents
Cahiez, Gerard,Luart, Denis,Lecomte, Fabien
, p. 4395 - 4398 (2007/10/03)
(Chemical equation presented) Alkyl- and arylmanganese reagents react with o-chloro or o-bromoaryl ketones to give the substituted ketones in high yields. The cross-coupling reaction is performed under mild conditions (-60 to +40°C, 30 min to 4 h) and tak
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.
Directed Lithiation of Tertiary β-Amino Benzamides
Comins, Daniel L.,Brown, Jack D.
, p. 3566 - 3572 (2007/10/02)
The directed ortho-lithiation-alkylation of several tertiary β-amino benzamides was studied.The ortho-substituted β-amino benzamides were hydrolyzed directly with 6 N hydrochloric acid, or by a three-step, one-pot reaction involving methylation, elimination, and treatment with aqueous acid. o-Toluic acid, 2-n-butylbenzoic acid, 2-methoxy-6-methylbenzoic aicd, and 4-methoxy-2-methylbenzoic acid were prepared by using this ortho-metalation-hydrolysis methodology.Ortho-lithiation and reaction with benzaldehyde or dimethylformamide followed by hydrolysis with aqueous acid gave lactones in good yield.Methanolysis of N-(4-methoxy-2-methyl benzoyl)-N'-methylpiperizine with sulfuric acid/methanol gave methyl 4-methoxy-2-methylbenzoate in 71percent yield.The conversion of tertiary benzamides into ketones and aldehydes was examined.Treatment of certain tertiary benzamides with alkyllithium reagents gave ketones, while reaction with a modified aluminum hydride reagent gave aldehydes
