3725-11-9Relevant academic research and scientific papers
Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism
Weweler, Jens,Younas, Sara L.,Streuff, Jan
supporting information, p. 17700 - 17703 (2019/11/13)
A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.
Palladium-Catalyzed Atom-Transfer Radical Cyclization at Remote Unactivated C(sp3)?H Sites: Hydrogen-Atom Transfer of Hybrid Vinyl Palladium Radical Intermediates
Ratushnyy, Maxim,Parasram, Marvin,Wang, Yang,Gevorgyan, Vladimir
supporting information, p. 2712 - 2715 (2018/03/02)
A novel mild, visible-light-induced palladium-catalyzed hydrogen atom translocation/atom-transfer radical cyclization (HAT/ATRC) cascade has been developed. This protocol involves a 1,5-HAT process of previously unknown hybrid vinyl palladium radical intermediates, thus leading to iodomethyl carbo- and heterocyclic structures.
Preparation method of bromomethylcyclohexane
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Paragraph 0010-0013, (2018/03/26)
The invention relates to a preparation method of bromomethylcyclohexane. The method comprises the steps that 1, alkali and cyclohexylmethanol are added into an organic solvent, then a compound in theformula (I) shown in the description is added dropwise, and esterification is conducted to obtain an organic-phase intermediate filtrate, wherein R is C1-12 alkyl or C1-12 halogen alkyl or C3-8 naphthenic base or phenyl or benzyl or aromatic hydrocarbon, X is a halogen atom, and the molar radio of the cyclohexylmethanol to the compound in the formula (I) is 1:1-1:2; 2, a bromide and a crown ethercatalyst are added into the obtained organic-phase intermediate filtrate for bromination reaction to obtain reaction liquid, then through filtering, abraum salt is removed, through rectification, a crude bromomethylcyclohexane product is obtained, and then through drying, a finished bromomethylcyclohexane product is obtained. The method has the advantages that high-salinity wastewater is reduced,reaction time is shortened, the reaction rate is improved, the production cost is reduced, and the product yield is improved.
Ionic liquid brush as an efficient and reusable heterogeneous catalytic assembly for the tosylation of phenols and alcohols in neat water
Feng, Simin,Li, Jing,Wei, Junfa
supporting information, p. 4743 - 4746 (2017/07/12)
A very efficient and reusable heterogeneous ionic liquid brush assembly was developed. The catalyst exhibits high catalytic activity for the tosylation of phenols and alcohols in neat water. Moreover, the catalyst shows outstanding stability and reusability, and it can be simply and effectively recovered and reused five times without noticeable loss of catalytic activity.
Design, synthesis and structure-activity relationships of (indo-3-yl) heterocyclic derivatives as agonists of the CB1 receptor. Discovery of a clinical candidate
Ratcliffe, Paul,Adam, Julia M.,Baker, James,Bursi, Roberta,Campbell, Robert,Clark, John K.,Cottney, Jean E.,Deehan, Maureen,Easson, Anna-Marie,Ecker, Daniel,Edwards, Darren,Epemolu, Ola,Evans, Louise,Fields, Ruth,Francis, Stuart,Harradine, Paul,Jeremiah, Fiona,Kiyoi, Takao,McArthur, Duncan,Morrison, Angus,Passier, Paul,Pick, Jack,Schnabel, Peter G.,Schulz, Jurgen,Steinbrede, Heinz,Walker, Glenn,Westwood, Paul,Wishart, Grant,Haes, Joanna Udo De
, p. 2541 - 2546 (2011/06/17)
We report an expansion of the structure-activity relationship (SAR) of a novel series of indole-3-heterocyclic CB1 receptor agonists. Starting from the potent but poorly soluble lead, 1, a rational approach was taken in order to balance solubility, hERG a
Cs2CO3 catalyzed rapid and efficient conversion of amines into sulfonamides; Alcohols and phenols into sulfonic esters
Reddy, M. B. Madhusudana,Pasha
experimental part, p. 1867 - 1875 (2011/10/11)
A simple and efficient method has been developed for the sulfonylation of several amines, alcohols, and phenols by p-toluenesulphonylchloride (p-TsCl) in the presence of catalytic amount of Cs2CO3 at 25C to obtain sulfonamides and sulfonic esters in very good yields. Cs2CO3 has been found to be highly efficient catalyst. Taylor & Francis Group, LLC.
A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
Meshram,Patil, Vishvanath D.
scheme or table, p. 1117 - 1121 (2009/05/27)
Cupric Oxide efficiently catalyzed the synthesis of sulfonamides and sulfonic esters. This method has been applied to a variety of substrates including nucleophilic and sterically-hindered amines, alcohols and phenols with excellent yields of sulfonamides and sulfonic esters. The remarkable selectivity under mild and neutral conditions of this commercially available inexpensive catalyst is an attractive feature of this method.
Aspects of the synthesis of an exceptionally preorganized self-immolative spacer-phenolate unit
Waibel, Michael,Zhang, Xiao-Bing,Hasserodt, Jens
experimental part, p. 318 - 324 (2009/06/27)
This study introduces a highly preorganized self-immolative spacer that is coupled to a nonfluorescent leaving group. The water-soluble compound can rapidly liberate a water-insoluble fluorescent precipitate by intramolecular attack of a free amine on a phenolic ester group via a six-membered transition state. One of the crucial steps in the synthesis of this molecule was a sterically very unfavored nucleophilic substitution to create a tertiary ether; this was optimized using model compounds. Another key challenge was deprotection by catalytic hydrogenation at low temperatures in order to furnish the hydroacetate of the free amine without further fragmentation. LC-MS and fluorescence studies showed that this compound collapsed instantaneously in methanol, as well as within a wide pH range in buffered aqueous media. Georg Thieme Verlag Stuttgart · New York.
Regioselective alkylation of hydroxysalicylaldehydes
Gichinga, Moses G.,Striegler, Susanne
supporting information; experimental part, p. 4917 - 4922 (2009/10/02)
Schiff-base ligands are often used as backbone ligands for mono- and dinuclear complexes that serve as catalysts during aerobic oxidation reactions. However, their water solubility is low and limits their applicability as catalysts to transform highly water-soluble biomolecules, such as carbohydrates or amino alcohols. A new method to regioselectively incorporate water solubility-promoting polyethylene glycol side chains into a frequently used aldehyde building block of Schiff-base ligands has been developed.
Kinetics and mechanism of the aminolysis of cycloalkylmethyl arenesulfonates
Oh, Hyuck Keun,Song, Se Jeong,Jo, Dong-Soo,Lee, Ikchoon
, p. 91 - 96 (2007/10/03)
Nucleophilic substitution reactions of cycloalkylmethyl arenesulfonates (CmH2n-1 CH2OSO2C6H4Z) with anilines (XC6H4NH2) in methanol at 65.0 °C were studied. The reactivity order (n=4>6>7>5) reflects largely the order of steric effect of the ring size (SEs term) except for n=5, which exhibits the least reactivity. This reversal of the order for n=5 is considered to result from large rate retardation due to polar effect of the ρ*σ* term. Application of the Taft equation to the rate data for n=5 and 6 gives ρ=17·4 and 5=2·3 with correlation coefficient of 0·90. The σ* values for n=4 and 7 are estimated to be - 0·23 and - 0·11, respectively. The positive ρxz values of ca 0·3 are consistent with previous results for the reactions at primary reaction centers.
