4746-09-2Relevant academic research and scientific papers
Diastereoselective and Stereodivergent Synthesis of 2-Cinnamylpyrrolines Enabled by Photoredox-Catalyzed Iminoalkenylation of Alkenes
Shen, Xu,Huang, Congcong,Yuan, Xiang-Ai,Yu, Shouyun
, p. 9672 - 9679 (2021/03/16)
A photoredox-catalyzed iminoalkenylation of γ-alkenyl O-acyl oximes has been developed. Readily available alkenylboronic acids serve as alkenylation reagents, leading to densely functionalized pyrrolines. Both (E)- and (Z)-cinnamylpyrrolines are accessible depending on the reaction solvent. In dichloromethane, (E)-cinnamylpyrrolines are produced through a photoredox-mediated single-electron-transfer process. In tetrahydrofuran, (Z)-cinnamylpyrrolines are generated by photocatalytic contra-thermodynamic E-to-Z isomerization of (E)-cinnamylpyrrolines though an energy-transfer pathway. Two stereocenters are established with complete diastereoselectivity and only one diastereomer is isolated.
Base-Catalyzed [1, n]-Proton Shifts in Conjugated Polyenyl Alcohols and Ethers
Molleti, Nagaraju,Martinez-Erro, Samuel,Carretero Cerdán, Alba,Sanz-Marco, Amparo,Gomez-Bengoa, Enrique,Martín-Matute, Belén
, p. 9134 - 9139 (2019/10/16)
The isomerization of dienyl alcohols and polyenyl alkyl ethers catalyzed by TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) under metal-free conditions is presented. Two reaction pathways have been observed. For dienyl alcohols, the reaction proceeds by a [1,3]
Catalyst-free chemoselective conjugate addition and reduction of α,β-unsaturated carbonyl compounds: Via a controllable boration/protodeboronation cascade pathway
Huang, Xi,Hu, Junjie,Wu, Mengying,Wang, Jiayi,Peng, Yanqing,Song, Gonghua
, p. 255 - 260 (2018/01/12)
A novel, efficient transition-metal-free and controllable boration/protodeboronation strategy has been developed for the chemoselective conjugate addition and 1,4-reduction of α,β-unsaturated carbonyl compounds. Without any metal-catalyst or base, a series of β-boration products of α,β-unsaturated carbonyl compounds was easily obtained in moderate to excellent yields in a mixed solvent of ethanol and water. The presence of a catalytic amount of Cs2CO3 can effectively induce further protodeboronation reaction towards 1,4-reduction products at higher reaction temperature. Therefore, by slightly changing the reaction conditions, the boration or reduction products of α,β-unsaturated carbonyl compounds can be controllably obtained. Mechanistic studies revealed that Cs2CO3 played the key role in activating the protodeboronation step. This transition-metal-catalyst-free and product controllable method provides a useful and eco-friendly tool for the highly chemoselective preparation of the β-boration products and 1,4-reduction products of α,β-unsaturated carbonyl compounds.
Cobalt-Catalyzed α-Alkylation of Ketones with Primary Alcohols
Zhang, Guoqi,Wu, Jing,Zeng, Haisu,Zhang, Shu,Yin, Zhiwei,Zheng, Shengping
supporting information, p. 1080 - 1083 (2017/03/14)
An ionic cobalt-PNP complex is developed for the efficient α-alkylation of ketones with primary alcohols for the first time. A broad range of ketone and alcohol substrates were employed, leading to the isolation of alkylated ketones with yields up to 98%. The method was successfully applied to the greener synthesis of quinoline derivatives while using 2-aminobenzyl alcohol as an alkylating reagent.
Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: Efficient construction of γ,δ-unsaturated ketones
Chen, Shu-Jie,Lu, Guo-Ping,Cai, Chun
supporting information, p. 11512 - 11514 (2016/01/15)
A highly regioselective protocol for the direct synthesis of γ,δ-unsaturated ketones from β-ketoacids and allylic alcohols was proposed and accomplished relying on the combination of [Ir(cod)Cl]2 and 10-camphorsulfonic acid via decarboxylative allylation.
Lithium tert-butoxide mediated α-alkylation of ketones with primary alcohols under transition-metal-free conditions
Liang, Yu-Feng,Zhou, Xin-Feng,Tang, Shi-Ya,Huang, Yao-Bing,Feng, Yi-Si,Xu, Hua-Jian
, p. 7739 - 7742 (2013/06/27)
LiOtBu was found to efficiently promote the α-alkylation reaction of ketones with primary alcohols, without the addition of any transition metal catalyst.
One-pot β-alkylation of secondary alcohols with primary alcohols catalyzed by ruthenacycles
Chang, Xu,Chuan, Low Wei,Yongxin, Li,Pullarkat, Sumod A.
experimental part, p. 1450 - 1455 (2012/04/10)
A ruthenacycle-catalyzed one-pot β-alkylation of secondary alcohols with primary alcohols is described. A survey of four C-N chelate ruthenacycles synthesized via the cyclometallation reaction of phenylmethanamine, N-methylphenylmethanamine, N,N-dimethylphenylmethanamine, and naphthalen-1-ylmethanamine with [(η6-C6H 6)RuCl2]2 was undertaken. All four complexes were found to be active with the phenylmethanamine-based ruthenacycle showing the best combination of reactivity and product selectivity among the four. An expanded scope of substrates was also studied with the inclusion of unsaturated primary alcohols. The reactivity trend observed gave insights into the role of hydrogen bonding in the catalytic mechanism involving transfer hydrogenation between the substrates and the transition metal catalyst.
Rapid and regioselective hydrogenation of α,β-unsaturated ketones and alkylidene malonic diesters using Hantzsch ester catalyzed by titanium tetrachloride
Che, Jun,Lam, Yulin
experimental part, p. 2415 - 2420 (2010/11/19)
A regioselective hydrogenation of α,β-unsaturated ketones and alkylidene malonic diesters using Hantzsch ester as the reducing agent and titanium tetrachloride as a catalyst is described. The short reaction times and mild reaction conditions are the advantages of this method. Georg Thieme Verlag Stuttgart New York.
Synthesis of early-transition-metal carbide and nitride nanoparticles through the urea route and their use as alkylation catalysts
Yao, Weitang,Makowski, Philippe,Giordano, Cristina,Goettmann, Frederic
scheme or table, p. 11999 - 12004 (2010/05/19)
The use of urea as either a carbon or a nitrogen source enabled the synthesis of various early-transition-metal nitride and carbide nanoparticles (TiN, NbN, Mo2N, 2N, NbCxN1-x, Mo2 C and WC). The abil
Lewis acid/CpRu dual catalysis in the enantioselective decarboxylative allylation of ketone enolates
Linder, David,Austeri, Martina,Lacour, Jerome
supporting information; experimental part, p. 4057 - 4061 (2009/12/06)
The addition of a Lewis acidic metal triflate salt Mg(OTf)2 as co-catalyst in the CpRu-catalyzed decarboxylative allylation of in situ-generated ketone enolates allows the reaction to proceed at lower temperature with higher regio- and enantios
