42524-30-1Relevant academic research and scientific papers
CuPd Nanoparticles as a Robust Catalyst for Electrochemical Allylic Alkylation
Guo, Xuefeng,Lin, Honghong,Muzzio, Michelle,Pang, Huan,Shen, Mengqi,Sun, Shouheng,Wei, Kecheng,Williard, Paul,Yin, Zhouyang,Yu, Chao
supporting information, p. 15933 - 15936 (2020/07/04)
An efficient CuPd nanoparticle (NP) catalyst (3 nm CuPd NPs deposited on carbon support) is designed for catalyzing electrochemical allylic alkylation in water/isopropanol (1:1 v/v) and 0.2 m KHCO3 solution at room temperature. The Pd catalysis was Pd/Cu composition-dependent, and CuPd NPs with a Pd/Cu ratio close to one are the most efficient catalyst for the selective cross-coupling of alkyl halides and allylic halides to form C?C hydrocarbons with product yields reaching up to 99 %. This NP-catalyzed electrochemical allylic alkylation expands the synthetic scope of cross-coupling reactions and can be further extended to other organic reaction systems for developing green chemistry electrosynthesis methods.
Copper-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Alkyl Fluorides and Grignard Reagents
Iwasaki, Takanori,Shimizu, Ryohei,Imanishi, Reiko,Kuniyasu, Hitoshi,Kambe, Nobuaki
, p. 9347 - 9350 (2015/08/06)
Copper complexes generated in situ from CuCl2, alkyl Grignard reagents, and 1,3-dienes play important roles as catalytic active species for the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides through C-F bond cleavage. The alkyl group is introduced to an internal carbon atom of the 1,3-diene regioselectively, thus giving rise to the branched terminal alkene product. Making the switch: A copper-hydride species, generated by the treatment of a copper salt with alkyl Grignard reagents, catalyzes the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides and Grignard reagents. The alkyl group of the alkyl fluoride is selectively introduced to an internal carbon atom of the 1,3-diene and the Grignard reagent acts as hydride source to give the branched terminal alkene, even in the presence of alkenes and alkynes.
Copper catalyzed magnesium-Barbier reaction for γ-selective alkyl-allyl coupling
Erdik, Ender,Ko?o?lu, Melike
, p. 4211 - 4214 (2008/02/08)
CuCN catalyzed alkyl-allyl coupling under magnesium-Barbier conditions occurs regioselectively and affords predominantly the γ-products in good to high yields. This one-pot CuCN catalyzed reaction utilising Mg, an alkyl halide and an allylic substrate in THF at room temperature provides an easy alternative to the classical CuCN catalyzed γ-allylation of alkyl Grignard reagents.
Regioselective opening of substituted (cyclopropylmethyl)lithiums derived from cyclopropylmethyl iodides
Charette, Andre B.,Naud, Julie
, p. 7259 - 7262 (2007/10/03)
Substituted cyclopropylmethanol derivatives were successfully opened with excellent regiocontrol by a three-step protocol. The resulting homoallylic carbanion could be trapped with a variety of electrophiles.
Substituent Effects on the Intramolecular Photochemical Reactions of Phenyl-Ethenyl Non-conjugated Bichromophoric Systems
Ellis-Davies, Graham C. R.,Gilbert, Andrew,Heath, Peter,Lane, Jon C.,Warrington, John V.,Westover, David L.
, p. 1833 - 1842 (2007/10/02)
The effects of substitution on the photochemistry of phenyl-ethenyl bichromophoric systems are reported.Methyl substitution at the 2-, 3-, 5-, and 1,1,2-positions in the pentene moiety of 5-phenylpent-1-ene reduces both reaction efficiency and selectivity but in contrast to intramolecular analogues the photoreaction of 3-phenethylcyclohexene is comparable with that of the corresponding cyclopentene.Incorporation of ester units in the connecting unit between the chromophores or on the ethene inhibits intramolecular cyclisation as does the presence of para OMe, CN, or COMe groups in 5-phenylpent-1-ene.In contrast reaction selectivity and efficiency are greatly promoted by ortho Me or OMe groups and the products reflect exlusive 1,3-cycloaddition.The presence of a para Me group in 5-phenylpent-1-ene leads to specific 2,6-intramolecular cyclisation but the reaction of the meta-Me derivative leads to four products derived from 1,3- and 1,5-intramolecular cycloaddition.The observations are discussed in terms of mechanisms of arene-ethene photoreactions and preferred conformations of the bichromophores.
A CONVENIENT COUPLING REACTION OF ALLYL ALCOHOLS WITH GRIGNARD REAGENTS USING 1-CHLORO-2-METHYL-N,N-TETRAMETHYLENEPROPENYLAMINE
Fujisawa, Tamotsu,Iida, Sachio,Yukizaki, Hisashi,Sato, Toshio
, p. 5745 - 5748 (2007/10/02)
1-Chloro-2-methyl-N,N-tetramethylenepropenylamine was found to be a good condensation reagent for a regioselective coupling reaction of allyl alcohols with Grignard reagents under mild conditions to afford olefinic products.
STEUERUNG DER REGIOSELEKTIVITAET BEI DER ADDITION VON BUT-2-ENYLZINK-VERBINDUNGEN AN STYROL
Lehmkuhl, Herbert,Nehl, Hans
, p. 131 - 136 (2007/10/02)
The addition of the butenyl-zinc bond in CH3CH=CHCH2ZnX derivatives VI-XII (X=n-C4H9, t-C4H9, Ph, cyclohexyl, Cl, OCH3, OPh) to styrene (XIII) affords a mixture of Zn -> Cprim and Zn -> Csec products.The regioselectivity can be contr
