55968-39-3Relevant academic research and scientific papers
Metal-free regioselective hydrochlorination of unactivated alkenes via a combined acid catalytic system
Liang, Shengzong,Hammond, Gerald B.,Xu, Bo
, p. 680 - 684 (2018)
A combined acid HCl/DMPU-acetic acid catalytic system was used in the hydrochlorination of a wide range of unactivated alkenes. This hydrochlorination strategy is remarkably greener than previous reported methods in terms of high atom efficiency, no toxic waste generated and metal-free process. The higher efficiency, compared with other commercially available HCl reagents, was augmented by the good regioselectivity and functionality tolerance found. A stepwise mechanism for this hydrochlorination process was proposed based on kinetic studies.
Ferric chloride–catalyzed deoxygenative chlorination of carbonyl compounds: A comparison of chlorodimethylsilane and dichloromethylsilane system
Xing, Bing-Han,Zhao, Xuan-Xuan,Qin, Yu-Jun,Zhang, Pu,Guo, Zhi-Xin
, p. 667 - 675 (2020/05/22)
Deoxygenative chlorination of carbonyl compounds using the HMe2SiCl/FeCl3/EtOAc and HMeSiCl2/FeCl3/EtOAc systems has been systemically investigated. The HMe2SiCl-FeCl3 system showed the advantages of good substrate applicability, mild reaction conditions, simple operation, low cost, and easy availability of raw materials. Also, it provided a simple and efficient synthesis route for carbonyl deoxychlorination via a one-pot method. Using the HMeSiCl2/FeCl3/EtOAc system, the β-methylchalcone derivative could be obtained in good yields in addition to obtaining the chlorinated compound. Finally, two plausible reaction routes were proposed to describe the formation of the chlorinated compound and the β-methylchalcone derivative.
Iron-catalysed enantioconvergent Suzuki-Miyaura cross-coupling to afford enantioenriched 1,1-diarylalkanes
Tyrol, Chet C.,Yone, Nang S.,Gallin, Connor F.,Byers, Jeffery A.
supporting information, p. 14661 - 14664 (2020/12/02)
The first stereoconvergent Suzuki-Miyaura cross-coupling reaction was developed to afford enantioenriched 1,1-diarylalkanes. An iron-based complex containing a chiral cyanobis(oxazoline) ligand framework was best to obtain enantioenriched 1,1-diarylalkanes from cross-coupling reactions between unactivated aryl boronic esters and benzylic chlorides. Enhanced yields were obtained when 1,3,5-trimethoxybenzene was used as an additive, which is hypothesized to extend the lifetime of the iron-based catalyst. Exceptional enantioselectivities were obtained with challenging ortho-substituted benzylic chlorides. This journal is
PYRIDAZINONES AND METHODS OF USE THEREOF
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Page/Page column 103, (2019/04/11)
Disclosed are compounds according to Formula (A), and related tautomers and pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating kidney diseases, using the compounds of Formula (A).
Nickel-catalyzed asymmetric reductive cross-coupling between vinyl and benzyl electrophiles
Cherney, Alan H.,Reisman, Sarah E.
supporting information, p. 14365 - 14368 (2014/12/11)
A Ni-catalyzed asymmetric reductive cross-coupling between vinyl bromides and benzyl chlorides has been developed. This method provides direct access to enantioenriched products bearing aryl-substituted tertiary allylic stereogenic centers from simple, stable starting materials. A broad substrate scope is achieved under mild reaction conditions that preclude the pregeneration of organometallic reagents and the regioselectivity issues commonly associated with asymmetric allylic arylation.
Catalytic asymmetric reductive acyl cross-coupling: Synthesis of enantioenriched acyclic α,α-disubstituted ketones
Cherney, Alan H.,Kadunce, Nathaniel T.,Reisman, Sarah E.
supporting information, p. 7442 - 7445 (2013/06/27)
The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a NiII/bis(oxazoline) catalyst in the presence of Mn0 as a stoichiometric reductant generates acyclic α,α-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.
Process for the preparation of substituted vinylbenzyl chloride
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, (2008/06/13)
An improved continous single step vapor phase process for the preparation of substituted vinylbenzyl chloride from substituted ethyltoluene is disclosed. In this process a substituted ethyltoluene is reacted with a halogen gas in the vapor phase, at elevated temperatures via a continuous feed process. Furthermore, this process achieves halogenation followed by dehydrohalogenation in a single pass through the reactor. There is also obtained a very high total selectivity to vinylbenzyl chloride and its precursors via this continuous process.
