30614-39-2Relevant academic research and scientific papers
Concerning the Role of Supercritical Carbon Dioxide in SN1 Reactions
Qiao, Yun X.,Theyssen, Nils,Eifert, Tobias,Liauw, Marcel A.,Franciò, Giancarlo,Schenk, Karolin,Leitner, Walter,Reetz, Manfred T.
supporting information, p. 3898 - 3902 (2017/03/27)
A series of SN1-type reactions has been studied under various conditions to clarify the role of supercritical carbon dioxide (scCO2) as reaction medium for this kind of transformations. The application of scCO2 did not result in higher yields in any of the experiments in comparison to those under neat conditions or in the presence of other inert compressed gases. High-pressure UV/Vis spectroscopic measurements were carried out to quantify the degree of carbocation formation of a highly SN1-active alkyl halide as a function of the applied solvent. No measureable concentration of carbocations could be detected in scCO2, just like in other low polarity solvents. Taken together, these results do not support the previously claimed activating effect via enhanced SN1 ionization due to the quadrupolar moment of the supercritical fluid.
Unprecedented alkylation of silicon enolates with alcohols via carbenium ion formations catalyzed by tin hydroxide-embedded montmorillonite
Tandiary, Michael Andreas,Asano, Masashi,Hattori, Taiki,Takehira, Satoshi,Masui, Yoichi,Onaka, Makoto
, p. 1925 - 1928 (2017/04/27)
The solid acid, tin hydroxide-embedded montmorillonite, catalyzes the unprecedented alkylation of various silicon enolates with primary, secondary and tertiary benzylic alcohols as well as secondary allylic alcohols. The acid catalysis of Sn-Mont was not only higher than that of the other ion-exchanged montmorillonites (M-Mont; M?=?H, Ti, Fe and Al), but also higher than that of the typical homogeneous acid catalysts such as BF3·OEt2, TMSOTf and TfOH.
Decarboxylative substitution of β-keto acids to benzylic alcohols catalyzed by molecular iodine
Han, Fuzhong,Zhang, Xinxin,Hu, Minggang,Jia, Lina
, p. 11466 - 11471 (2015/12/04)
An efficient method for molecular iodine catalyzed decarboxylative substitution of β-keto acids with benzylic alcohols under mild conditions has been described and valuable α-functionalized ketones were obtained in good to excellent yields.
Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si-X Bond Activation by Halogen Bonding
Saito, Masato,Tsuji, Nobuya,Kobayashi, Yusuke,Takemoto, Yoshiji
supporting information, p. 3000 - 3003 (2015/06/30)
The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields. Detailed control experiments and mechanistic studies revealed that the XB interaction was crucial for the reaction. The application of this coupling reaction is also described.
Aluminum triflate as a powerful catalyst for direct amination of alcohols, including electron-withdrawing group-substituted benzhydrols
Ohshima, Takashi,Ipposhi, Junji,Nakahara, Yasuhito,Shibuya, Ryozo,Mashima, Kazushi
supporting information, p. 2447 - 2452 (2012/11/07)
Direct aminations of allylic alcohols, benzylic alcohols, and benzhydrols with electron-withdrawing (F, Br, I, NO2, or CN) substituents were efficiently catalyzed by aluminum triflate [Al(OTf)3] to afford the corresponding biarylamines in high yield, and the dibromo-substituted product was further transformed into letrozole. Copyright
Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon-nitrogen and carbon-carbon bonds
Yang, Cui-Feng,Wang, Jian-Yong,Tian, Shi-Kai
supporting information; experimental part, p. 8343 - 8345 (2011/09/16)
An efficient decarboxylative alkylation reaction of β-keto acids with N-benzylic or N-allylic sulfonamides has been developed, for the first time, through sequential cleavage of carbon-nitrogen and carbon-carbon bonds in the presence of 10 mol% of FeCl3.
Oxidation of Tricarbonyl(η1,η2-but-3-en-1-yl)iron(0) and Tricarbonyl(η3-allyl)iron(0) Anion Complexes with Dioxygen
Hwu, Chong-Chen,Yeh, Ming-Chang P.
, p. 825 - 832 (2007/10/03)
The addition of reactive carbanions to tricarbonyl(η4-1,3-diene)iron()) complexes proceeded at -78 deg C to give putative triacarbonyl(η1,η2-but-3-en-1-yl)iron(0) anion complexes and at 25 deg C to produce postulated triabarbonyl(η3-allyl)iron(0) anion complexes; trapping of reactive intermediates with dioxygen produced γ,δ-unsaturated acids and allylic alcohols, respectively.Key Words: Diene iron complex; γ,δ-Unsaturated acids; Allylic alcohols.
