18916-11-5Relevant academic research and scientific papers
Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex
Hashimoto, Toru,Funatsu, Kei,Ohtani, Atsufumi,Asano, Erika,Yamaguchi, Yoshitaka
, (2019/07/10)
A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.
Iron-Catalyzed Grignard Cross-Couplings with Allylic Methyl Ethers or Allylic Trimethylsilyl Ethers
Seto, Chika,Otsuka, Takeshi,Takeuchi, Yoshiki,Tabuchi, Daichi,Nagano, Takashi
supporting information, p. 1211 - 1214 (2018/03/26)
We have found that cross-coupling between aryl Grignard reagents and allylic methyl ethers proceeded well in the presence of a catalytic amounts of Fe(acac) 3 to afford the corresponding allylic substitution products in good yields. Under the same conditions, allylic trimethylsilyl ethers also reacted with Grignard reagents to give the corresponding cross-coupling products.
Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
Wang, Gaonan,Gan, Yi,Liu, Yuanhong
supporting information, p. 916 - 920 (2018/09/22)
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.
Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents
Yang, Bo,Wang, Zhong-Xia
, p. 4542 - 4549 (2017/05/12)
Nickel-catalyzed cross-coupling of allyl alcohols with aryl- and alkenylzinc chlorides through C-O bond cleavage was performed. Reaction of (E)-3-phenylprop-2-en-1-ol and 1-aryl-prop-2-en-1-ols with aryl- or alkenylzinc chlorides gave linear cross-coupling products. Reaction of 1-phenyl- or 1-methyl-substituted (E)-3-phenylprop-2-en-1-ol with aryl- or alkenylzinc chlorides resulted in 3-aryl/alkenyl-substituted (E)-(prop-1-ene-1,3-diyl)dibenzenes or 3-aryl/alkenyl-substituted (E)-(but-1-enyl)benzene. Reaction of allyl alcohol with p-Me2NC6H4ZnCl resulted in a mixture of normal coupling product 4-allyl-N,N-dimethylaniline and its isomerized product N,N-dimethyl-4-(prop-1-en-1-yl)aniline.
Photochemical Heck benzylation of styrenes catalyzed by Na[FeCp(CO)2]
Waldhart, Greyson W.,Mankad, Neal P.
supporting information, p. 171 - 174 (2015/03/05)
Iron-catalyzed Heck coupling of benzyl chlorides and styrenes proceeds under photochemical conditions using the well-known anionic complex, [FeCp(CO)2]- (Fp-), as a catalyst. The reaction likely proceeds through the established SN2 mechanism for Fp- alkylation, followed by styrene migratory insertion and β-hydride elimination steps that are enabled by photochemical CO dissociation.
Copper-Catalyzed Alkenylation of Alcohols with β-Nitrostyrenes via a Radical Addition-Elimination Process
Guo, Sheng-Rong,Yuan, Yan-Qin
supporting information, p. 1961 - 1968 (2015/09/01)
A new method for the preparation of allylic alcohol derivatives has been developed via a radical mechanism using DTBP as the radical initiator promoted by copper salt. The C(sp3)-H bond in various alcohols, toluene derivatives, and alkanes were successfully converted into C-C bonds to yield the desired products in moderate to good yields.
Copper-catalyzed oxidative alkenylation of C(sp3)-H bonds via benzyl or alkyl radical addition to β-nitrostyrenes
Guo, Shengrong,Yuan, Yanqin,Xiang, Jiannan
supporting information, p. 3093 - 3097 (2015/04/14)
A new method for the preparation of (E)-β-alkylstyrene derivatives has been developed via the addition of a benzyl or alkyl radical to β-nitrostyrenes using di-tert-butyl peroxide (DTBP) as the oxidant in the presence of Cu powder catalyst. The C-H bonds in various toluene derivatives, ethers, alkanes and alcohols were successfully converted into C-C bonds to yield the corresponding (E)-β-alkylstyrene derivatives in moderate to good yields.
Allyl-aryl coupling of allylic carbonates with arylboronic acids catalyzed by palladium nanoparticles in ionic liquid
Xu, Jing,Zhai, Xing,Wu, Xue,Zhang, Yong Jian
supporting information, p. 1712 - 1717 (2015/03/30)
A practical and greener process for the allyl-aryl coupling of allylic carbonates with arylboronic acids catalyzed by in situ generated palladium nanoparticles (PdNPs) in ionic liquid (IL) has been described. The PdNPs showed high catalytic activity for the coupling reaction in the IL to afford allyl-aryl coupling products in good to high yields with complete regio- and E/Z selectivities. The PdNPs were readily immobilized in the IL phase and the catalyst can be reused several times without significant loss of catalytic activity and stereospecificity.
A simple and direct method for the palladium-catalyzed oxidative coupling of unactivated allylarenes with classic arenes
Jin, Weiwei,Wong, Wing-Tak,Law, Ga-Lai
, p. 1599 - 1603 (2014/06/24)
An efficient route to engineer vinylarene structures by the Pd II-catalyzed oxidative coupling of unactivated allylarenes with classic arenes was developed. The methodology features the use of unactivated allylarenes with no prefunctionalization and classic arenes without installed directing groups. A variety of vinylarenes and their saturated derivatives were obtained. They make a great couple: An efficient route to engineer vinylarene structures by PdII-catalyzed oxidative coupling of unactivated allylarenes with classic arenes is developed. The methodology features the use of unactivated allylarenes with no prefunctionalization and classic arenes without installed directing groups. A variety of vinylarenes and their saturated derivatives are obtained.
Iron-catalyzed allylic arylation of olefins via C(sp3)-H activation under mild conditions
Sekine, Masaki,Ilies, Laurean,Nakamura, Eiichi
, p. 714 - 717 (2013/04/10)
An aryl Grignard reagent in the presence of mesityl iodide converts an allylic C-H bond of a cycloalkene or an allylbenzene derivative into a C-C bond in the presence of a catalytic amount of Fe(acac)3 and a diphosphine ligand at 0 C. The stereo- and regioselectivity of the reaction, together with deuterium labeling experiments, suggest that C-H bond activation is the slow step in the catalytic cycle preceding the formation of an allyliron intermediate.
