28047-23-6Relevant articles and documents
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.
Iterative Synthesis of Pluripotent Thioethers through Controlled Redox Fluctuation of Sulfur
Colas, Kilian,Mendoza, Abraham
, p. 1329 - 1333 (2018/06/13)
Target- and diversity-oriented syntheses are based on diverse building blocks, whose preparation requires discrete design and constructive alignment of different chemistries. To enable future automation of the synthesis of small molecules, we have devised a unified strategy that serves the divergent synthesis of unrelated scaffolds such as carbonyls, olefins, organometallics, halides, and boronic esters. It is based on iterations of a nonelectrophilic Pummerer-type C-C coupling enabled by turbo -organomagnesium amides that we have recently reported. The pluripotency of sulfur allows the central building blocks to be obtained by regulating C-C bond formation through control of its redox state.
Intermolecular Pummerer Coupling with Carbon Nucleophiles in Non-Electrophilic Media
Colas, Kilian,Martín-Montero, Raúl,Mendoza, Abraham
supporting information, p. 16042 - 16046 (2017/11/21)
A new Pummerer-type C?C coupling protocol is introduced based on turbo-organomagnesium amides, which unlike traditional Pummerer reactions, does not require strong electrophilic activators, engages a broad range of C(sp3)-, C(sp2)-, and C(sp)-nucleophiles, and seamlessly integrates with C?H and C?X magnesiation. Given the central character of sulfur compounds in organic chemistry, this protocol allows access to unrelated carbonyls, olefins, organometallics, halides, and boronic esters through a single strategy.
Iron catalyzed halogenation of benzylic aldehydes and ketones
Savela, Risto,W?rn?, Johan,Murzin, Dmitry Yu.,Leino, Reko
, p. 2406 - 2417 (2015/04/14)
A simple and efficient iron-catalyzed method for chlorination of aromatic carbonyl compounds is reported. By using 4-10 mol% Fe(iii) oxo acetate catalyst, prepared by solid state atmospheric oxidation of Fe(ii) acetate, in combination with triethylsilane and chlorotrimethylsilane, hydrosilylation of benzylic carbonyl compounds with subsequent chlorination is achieved within a few hours at room temperature. This new method is mild and rapid compared to the conventional two step approach involving reduction and chlorination reactions in separate stages. Development of synthetic methodology is also supplemented here by kinetic investigation of the reaction mechanism, which supports the tentative mechanisms suggested previously for similar reactions. This journal is
HETEROCYCLIC COMPOUND AND H1 RECEPTOR ANTAGONIST
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, (2013/04/13)
A heterocyclic compound useful as an antiallergic agent is provided. A compound represented by the following formula (1) or a salt thereof: wherein the ring A is a homocyclic or heterocyclic ring; the ring B is a heterocyclic ring which contains G and nitrogen atom N as constituent atoms thereof, wherein G is CH or N; R1 is a carbonyl group or an alkylene group; R2a and R2b are an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group; X is an oxygen atom or a sulfur atom; Z is a hydroxyl group, an alkoxy group, a cycloalkyloxy group, an aryloxy group, an aralkyloxy group, an amino group, or an N-substituted amino group; and n is 0 or 1; with the proviso that when the ring A is a benzene ring or when the ring B is a piperazine ring, R1 is an alkylene group which may have a substituent.
EFFICIENT PRODUCTION OF HETEROLOGOUS PROTEINS USING MANNOSYL TRANSFERASE INHIBITORS
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, (2009/12/27)
Compounds and methods are described for producing protein compositions having reduced amounts of O-linked glycosylation. The method includes producing the protein in cells cultured in the presence of certain benzylidene thiazolidinediones inhibitors of Pm
A new method for alkylation of aromatic aldehydes using alkylboron chloride derivatives in the presence of oxygen
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 3243 - 3248 (2007/10/03)
Reactions of aromatic aldehydes with alkylboron chloride derivatives in the presence of oxygen have been investigated. Dialkylboron chlorides react with aryl aldehydes to produce arylalkylmethanols in good to excellent yields. Under the same reaction conditions, alkylboron dichlorides lead to the formation of arylalkyl chlorides.
Alkylation of aromatic aldehydes with alkylboron chloride derivatives
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 1663 - 1670 (2007/10/03)
The reaction of aryl aldehydes with alkylboron chlorides has been investigated. Monoalkylboron dichlorides react with aryl aldehydes in hexane under reflux conditions to give a mixture of dichloroarylmethane and benzyl chloride. Under the same reaction conditions, dialkylboron chlorides lead to formation of a mixture of benzyl chloride and the chloroalkylation product. In the presence of a base such as 2,6-lutidine, the reactions of monoalkylboron dichlorides with aryl aldehydes yield small amounts of the desired alkylation products at room temperature. Dialkylboron chlorides react with aryl aldehydes in hexane in the presence of base to generate the corresponding arylalkylmethanols in good yields.
Chloroalkylation of aryl aldehydes using alkylboron dichlorides in the presence of oxygen
Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong
, p. 6239 - 6241 (2007/10/03)
Reactions of aryl aldehydes with alkylboron dichlorides in the presence of oxygen at room temperature produces arylalkyl chlorides in good to excellent yields.
Absolute kinetics of phenylchlorocarbene C-H insertion reactions
Moss, Robert A.,Yan, Shunqi
, p. 9381 - 9384 (2007/10/03)
Absolute rate constants, activation parameters, a kinetic isotope effect, and hybrid density functional theory computational results are presented for various C-H insertion reactions of PhCCl.