1569-44-4Relevant articles and documents
Predicting and optimizing asymmetric catalyst performance using the principles of experimental design and steric parameters
Harper, Kaid C.,Sigman, Matthew S.
, p. 2179 - 2183 (2011)
Using a modular amino acid based chiral ligand motif, a library of ligands was synthesized systematically varying the substituents at two positions. The effects of these changes on ligand structure were probed in the enantioselective allylation of benzald
Hydroalumination of terminal β-acetylene alcohols with lithium aluminum hydride
Garibyan,Makaryan,Ogannisyan,Chobanyan
, p. 267 - 272 (2016/04/20)
Hydrogenation of terminal β-acetylene alcohols with lithium aluminum hydride in THF has afforded homoallylic alcohols. Decomposition of the intermediate organoaluminum complex with deuterated water, iodine, or pyridinium dibromide has evidenced about the non-regioselective hydride attack at the triple bond.
A Green approach for allylations of aldehydes and ketones: Combining allylborate, mechanochemistry and lanthanide catalyst
De Souza, Viviane P.,Oliveira, Cristiane K.,De Souza, Thiago M.,Menezes, Paulo H.,Alves, Severino,Longo, Ricardo L.,Malvestiti, Ivani
, (2016/12/02)
Secondary and tertiary alcohols synthesized via allylation of aldehydes and ketones are important compounds in bioactive natural products and industry, including pharmaceuticals. Development of a mechanochemical method using potassium allyltrifluoroborate salt and water, to successfully perform the allylation of aromatic and aliphatic carbonyl compounds is reported for the first time. By controlling the grinding parameters, the methodology can be selective, namely, very efficient for aldehydes and ineffective for ketones, but by employing lanthanide catalysts, the reactions with ketones can become practically quantitative. The catalyzed reactions can also be performed under mild aqueous stirring conditions. Considering the allylation agent and its by-products, aqueous media, energy efficiency and use of catalyst, the methodology meets most of the green chemistry principles.
Tin mediated Barbier type allylation in ionic liquids
Slaton, Rahiem,Petrone, Adam,Manchanayakage, Renuka
experimental part, p. 5073 - 5076 (2011/10/09)
The Barbier type allylation of carbonyl compounds is a useful organic transformation as the resultant homoallylic alcohols are important building blocks for many biologically active molecules. Tin mediated Barbier allylation of different carbonyl compounds in room temperature ionic liquid, [BMIM][BF 4] afforded the corresponding homoallylic alcohols in good to excellent yields. The ionic liquid was successfully recycled and reused in allylation reactions.
Allylation of carbonyl compounds mediated by Aluminum/Fluoride salts in water
Yuan, Shizhen,Liu, Jin,Xu, Ling,Zhu, Shaofeng
experimental part, p. 578 - 582 (2010/10/04)
A novel mediator (Al/KF) has been developed and employed in the Barbier-type alkylations of various aldehydes and ketones with alkyl halide in water. The carbonyl compounds could be effectively converted into corresponding homoallylic alcohol in good yiel
Synthesis of homoallylic alcohols from ketones in water
Wang, Jun,Yuan, Gu
, p. 401 - 405 (2007/10/03)
Homoallylic alcohols have been prepared in good yields by allylation of ketones with allyl bromide in the presence of stannous chloride dihydrate, zinc iodide, and ammonium chloride in water. Copyright Taylor & Francis LLC.
Barbier-type reaction mediated with tin nano-particles in water
Zha, Zhenggen,Qiao, Shu,Jiang, Jiaoyang,Wang, Yusong,Miao, Qian,Wang, Zhiyong
, p. 2521 - 2527 (2007/10/03)
Tin nano-particles are employed in the Barbier-type allylation reaction of carbonyl compounds in water to afford the corresponding homoallylic alcohols in good yields. The in situ generated allylation intermediates, allyltin(II) bromide and diallyltin dib
Organometallic reactions in aqueous media: The allylations of carbonyl compounds mediated in Zn/CdSO4 and Zn/SnCl2 bimetal systems
Zhou, Cunliu,Zhou, Yuqing,Jiang, Jiaoyang,Xie, Zhen,Wang, Zhiyong,Zhang, Jiahai,Wu, Jihui,Yin, Hao
, p. 5537 - 5540 (2007/10/03)
Zn/CdSO4 and Zn/SnCl2 bimetal systems were employed in the allylations of aldehydes or ketones in distilled water to afford the corresponding homoallylic alcohols in good yields. Also, the chemoselectivity was studied under the same
Novel ultrasonication-assisted carbonyl allylation mediated by SnCl 2 in water
Wang, Jun,Yuan, Gu,Dong, Chang-Qing
, p. 286 - 287 (2007/10/03)
Under ultrasonication, it was found that SnCl2 could efficiently mediate the aqueous Barbier reactions between carbonyl compounds and allyl bromide to give the corresponding homoallylic alcohols in high yields without using any Lewis acid catalyst.
SnCl2-mediated carbonyl allylation in fully aqueous media
Tan, Xiang-Hui,Hou, Yong-Quan,Huang, Chao,Liu, Lei,Guo, Qing-Xiang
, p. 6129 - 6136 (2007/10/03)
Systematic studies were performed on SnCl2-mediated carbonyl allylation reaction between aldehydes and allyl halides in fully aqueous media. Totally three valuable reaction systems were discovered, which were SnCl 2/CuCl2, SnCl2/TiCl3, and SnCl 2/PdCl2. They all provided good to excellent yields in the allylation of aliphatic and aromatic aldehydes under very mild and convenient conditions. SnCl2, by itself, was also found to be effective for the allylation reaction when allyl bromide was employed. However, the SnCl 2-only reaction could only tolerate very small amount of water as the solvent. The SnCl2/CuCl2, SnCl2/TiCl 3, and SnCl2/PdCl2-mediated reactions exhibited good regioselectivity favoring the γ-adduct when cinnamyl halides were employed as the allylation reagent. The same reactions with cinnamyl halides also showed good diastereoselectivity favoring the anti-product. Mechanistic studies using proton NMR techniques suggested that the additive (i.e., CuCl 2, TiCl3, PdCl2) could accelerate the formation of allyltin intermediate, but this step was shown not to be the most important for the allylation. Thus we proposed that the Lewis acid catalysis effect exerted by the additive was the main reason for the observed reactivity enhancement.