79786-73-5Relevant academic research and scientific papers
Carbonyl allylation of aldehydes and ketones with allylic chlorides catalyzed by immobilization of palladium in MCM-41
Zhao, Hong,Peng, Jian,Xiao, Ruian,Hao, Wenyan,Cai, Ming-Zhong
experimental part, p. 2030 - 2034 (2011/06/19)
The heterogeneous carbonyl allylation of aldehydes and ketones with allylic chlorides was achieved in DMF using SnCl2 as reducing agent at 25-40 °C in the presence of a 3-(2-aminoethylamino)propyl-functionalized MCM-41-immobilized palladium(II) complex [MCM-41-2N-Pd(II)], yielding a variety of homoallylic alcohols in good to high yields. This heterogeneous palladium catalyst exhibited higher activity than (N-propylethylenediamine)PdCl 2 and can be recovered and recycled by a simple filtration of the reaction solution and used for at least 5 consecutive trials without any decreases in activity.
Mild and general zinc-alkoxide-catalyzed allylations of ketones with allyl pinacol boronates
Fandrick, Keith R.,Fandrick, Daniel R.,Gao, Joe J.,Reeves, Jonathan T.,Tan, Zhulin,Li, Wenjie,Song, Jinhua J.,Lu, Bruce,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 3748 - 3751 (2010/11/18)
A general and efficient zinc-alkoxide-catalyzed allylation of a diverse array of ketones with allyl boronates is presented. The methodology is effective with 2 mol % of catalyst and with relatively short reaction times. Studies of the key exchange process are presented, which support a cyclic transition state for the boron to zinc exchange.
Synthesis of homoallylic alcohols by allylation of aldehydes and ketones catalysed by a mesoporous material (mcm-41)-supported cyano palladium complex
Yao, Fang,Huang, Bin,Cai, Mingzhong
experimental part, p. 366 - 369 (2009/12/25)
A variety of homoallylic alcohols has been conveniently synthesised in good to high yields by the allylation of aldehydes and ketones with allylic chlorides catalysed by an MCM-41-supported cyano palladium complex in DMF using SnCl2 as reducing agent. This polymeric palladium complex can be recovered and reused with some loss of activity.
An efficient method for allylation of ketones with tetra-allylstannane
Kamble, Rajesh M,Singh, Vinod K
, p. 7525 - 7526 (2007/10/03)
A variety of ketones undergo an allylation reaction with tetra-allyltin in the presence of a catalytic amount of Cu(OTf)2 or Sn(OTf)2. The method was found to be superior to most of the known methods, which are efficient only with al
Indium-mediated allylation reactions of α-chlorocarbonyl compounds and preparation of allylic epoxides
Shin, Jeong Ah,Choi, Kyung Il,Pae, Ae Nim,Koh, Hun Yeong,Kang, Han-Young,Cho, Yong Seo
, p. 946 - 948 (2007/10/03)
Indium-mediated allylation of α-chlorocarbonyl compounds with various allyl bromides in aqueous media gave the corresponding homoallylic chlorohydrins, which could be transformed into the corresponding epoxides in the presence of a base. These reactions w
Tellurium-zinc exchange between organotelluronium salts and diethylzinc - Reaction of the In Situ generated mixed diorganozinc with carbonyl compounds
Huang, Wen-Hua,Huang, Yao-Zeng,Dai, Li-Xin
, p. 6953 - 6956 (2007/10/03)
Organotelluronium salts undergo a smooth tellurium-zinc exchange reaction with diethylzinc. The in situ generated mixed diorganozinc reagents reacted with carbonyl compounds to give secondary or tertiary alcohols in good to excellent yields.
Carbonyl allylation catalyzed by silica-bound poly-γ- cyanopropylsiloxane palladium complex
Cai, Ming-Zhong,Song, Cai-Sheng,Huang, Xian
, p. 3087 - 3093 (2007/10/03)
The silica-bound poly-γ-cyanopropylsiloxane palladium complex has been found to catalyze the allylation of carbonyl compounds via the formation of π-allylpalladium complexes, using allyl chloride or allyl acetate as allylating agent and SnCl2 as reducing agent. This polymeric palladium complex is stable and can be reused.
Lewis Acid-Promoted Addition of Allyl(cyclopentadienyl)iron(II) Dicarbonyl To Unactivated Ketones
Jiang, Songchun,Turos, Edward
, p. 4639 - 4642 (2007/10/02)
The Lewis acid-promoted addition of allyl(cyclopentadienyl)iron(II) dicarbonyl (1) to unactivated ketones provides zwitterionic iron-olefin complexes 5 as isolable salts.Treatment of these complexes with NaI in wet acetone affords homoallylic alcohols in
β-Substituted Organolithium Compounds from Chlorohydrins: Application to the Direct Synthesis of Bifunctionalized Organic Cpmpounds
Barluenga, Jose,Florez, Josefa,Yus, Miguel
, p. 3019 - 3026 (2007/10/02)
The reaction of different chlorohydrins with n-butyl-lithium at -78 deg C followed by metallation wiht lithium naphthalenide at the same temperature leads to very reactive organolithium compounds bearing an alkoxide function at the β-position with respect to metal.The reaction of these intermediates with several electriphiles leads to mono- as well as bi-functionalized organic compounds.Thus, treatment of these dianions with deuterium oxide, oxygen, carbon dioxide, benzyl bromide, dimethyl disulphide, and carbonyl compounds, gave 2-deuterioalcohols, 1,2-diols, β-hydroxy-acids, 2-benzyl alcohols, 2-hydroxy-thioethers, and 1,3-diols respectively.The preparation of β-substituted organolithium derivatives can be alternatively carried out starting from α-chloroketones by the same procedure.When the lithium atom is linked to a secondary carbon atom the dianions are very unstable and decompose, even at -100 deg C, by β-elimination yielding the corresponding olefins.
