16170-45-9Relevant academic research and scientific papers
Pd-Catalyzed Allylic Isocyanation: Nucleophilic N-Terminus Substitution of Ambident Cyanide
Yurino, Taiga,Tani, Ryutaro,Ohkuma, Takeshi
, p. 4434 - 4440 (2019)
In the presence of catalytic amount of Pd(OAc)2, allylic phosphates reacted with trimethylsilyl cyanide (TMSCN) to afford the corresponding allylic isonitriles exclusively. No allylic nitriles, which are selectively obtained in the traditional
From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water
Martins, Nayara Silva,ángel, Alix Y. Bastidas,Anghinoni, Jo?o M.,Lenard?o, Eder J.,Barcellos, Thiago,Alberto, Eduardo E.
supporting information, p. 87 - 93 (2021/11/03)
The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).
Preparation method of aryl acetonitrile derivative
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Paragraph 0083-0086, (2021/10/20)
The invention relates to a continuous nucleophilic addition and beta-fluorine elimination reaction method of 2,2-difluoroolefin and ammonia water in a catalyst-free and additive-free system. The method comprises the following steps: adding a 2,2-difluoroolefin compound, ammonia water and a solvent into a Schlenk reaction flask, and conducting stirring and reacting at a certain temperature in an air atmosphere to obtain the product aryl acetonitrile derivative.
Dual electrocatalysis enables enantioselective hydrocyanation of conjugated alkenes
Song, Lu,Fu, Niankai,Ernst, Brian G.,Lee, Wai Hang,Frederick, Michael O.,DiStasio, Robert A.,Lin, Song
, p. 747 - 754 (2020/07/03)
Chiral nitriles and their derivatives are prevalent in pharmaceuticals and bioactive compounds. Enantioselective alkene hydrocyanation represents a convenient and efficient approach for synthesizing these molecules. However, a generally applicable method featuring a broad substrate scope and high functional group tolerance remains elusive. Here, we address this long-standing synthetic problem using dual electrocatalysis. Using this strategy, we leverage electrochemistry to seamlessly combine two canonical radical reactions—cobalt-mediated hydrogen-atom transfer and copper-promoted radical cyanation—to accomplish highly enantioselective hydrocyanation without the need for stoichiometric oxidants. We also harness electrochemistry’s unique feature of precise potential control to optimize the chemoselectivity of challenging substrates. Computational analysis uncovers the origin of enantio-induction, for which the chiral catalyst imparts a combination of attractive and repulsive non-covalent interactions to direct the enantio-determining C–CN bond formation. This work demonstrates the power of electrochemistry in accessing new chemical space and providing solutions to pertinent challenges in synthetic chemistry. [Figure not available: see fulltext.]
Method for synthesizing diaryl pyrrole compound
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Paragraph 0083-0089; 0124; 0133; 0143; 0148, (2018/07/06)
The invention relates to a method for synthesizing a diaryl pyrrole compound. The method comprises a reaction route shown in the specification. The method comprises the following steps: S1, in the presence of a palladium catalyst, organic ligand, an oxidant and an acid compound, enabling a compound of formula (I) and a compound of formula (2) to react in an organic solvent, and performing aftertreatment after the reaction is completed so as to obtain a compound of formula (3); S2, in the organic solvent, enabling the compound of formula (3) to be subjected to a self-cyclization reaction in thepresence of the oxidant, and performing aftertreatment after the reaction is completed so as to obtain a compound of formula (4); S3, in the presence of nitrogen, enabling the compound of formula (4)and a compound of formula (5) to react in the solvent in the presence of the palladium catalyst, the organic ligand, the oxidant and the acid compound, and performing aftertreatment after the reaction is completed so as to obtain a compound of formula (6). By adopting the method, different steps are creatively optimized with multiple technical characteristics, completely new synthesis methods andsynthesis routes are provided for preparation of the compound, and good industrial prospects and potential application values can be achieved.
Synthetic method for diaryl furan compound
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Paragraph 0072-0077; 0106-0114; 0117-0123; 0125-0132; 0134, (2018/07/07)
The invention relates to a synthetic method for a diaryl furan compound with a formula (6) which is described in the specification. The synthetic method has a reaction route as shown in the specification. The synthetic method comprises the following steps: S1: allowing a compound with a formula (1) and a compound with a formula (2) to react in an organic solvent in the presence of a palladium catalyst, an organic ligand, an oxidant and an acidic compound, and after completion of the reaction, carrying out post-treatment so as to obtain a compound with a formula (3); S2, allowing the compound with the formula (3) to generate a self-cyclization reaction in an organic solvent in the presence of a catalyst, and after completion of the reaction, carrying out post-treatment so as to obtain a compound with a formula (4); and S3, allowing the compound with the formula (4) and a compound with a formula (5) to react in a solvent in the presence of a palladium catalyst, an organic ligand and an acidic compound at the atmosphere of oxygen, and after completion of the reaction, carrying out post-treatment so as to obtain a compound with a formula (6). The method provided by the invention realizes creative optimization in a plurality of technical characteristics through all steps, provides a novel synthetic method and a synthetic route for preparation of the compound, and has good industrialprospects and potential application values.
Epoxy-containing skeleton nitrile compound and synthesis method thereof
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Paragraph 0077-0080; 0117; 0126; 0136; 0141, (2018/07/30)
The invention relates to an epoxy-containing skeleton nitrile compound as shown in the following formula (4) and a synthesis method thereof. The synthesis method adopts the following reaction route: FORMULA, and comprises the following steps: S1: reacting a compound of a formula (1) with a compound of formula (2) in an organic solvent in the presence of a palladium catalyst, an organic ligand, anoxidizing agent and an acidic compound, performing post-treatment after finishing reaction to obtain a compound of formula (3); and S2: performing self-cyclization reaction on the compound of formula(3) in the organic solvent in the presence of the oxidizing agent, performing post-treatment after finishing reaction to obtain a compound of formula (4). The method creatively optimizes multiple technical features in each step so as to provide a novel synthesis method and synthesis route for preparation of such compounds and have excellent industrial prospects and potential application values.
Method for synthesizing pyrrole derivative
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Paragraph 0087; 0088; 0089; 0090, (2018/07/07)
The invention relates to a method for synthesizing a pyrrole derivative represented by a formula (6) shown in the description. The synthesis method has a reaction route shown in the description. The synthesis method comprises the following steps: S1: subjecting a compound represented by a formula (3) shown in the description to a self-cyclization reaction in the presence of an oxidant in an organic solvent, and carrying out aftertreatment after the reaction ends, so as to obtain a compound represented by a formula (4) shown in the description; and S2: subjecting the compound represented by theformula (4) and a compound represented by a formula (5) shown in the description to a reaction in the presence of a palladium catalyst, an organic ligand and an acidic compound in a solvent in a nitrogen atmosphere, and carrying out aftertreatment after the reaction ends, so as to obtain a compound represented by a formula (6) shown in the description. According to the method, through creativelyoptimizing a plurality of technical features of each step, a bran-new synthesis method and synthesis route are provided for preparing this kind of compounds, and thus, the method has a good industrialization prospect and a potential application value.
A synthetic method of furan derivatives
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Paragraph 0075-0078, (2018/05/30)
The invention relates to a synthetic method of furan derivatives shown as a formula (6) as follows. The synthetic route of the method is shown in the specification. The method includes S1) allowing acompound shown as a formula (3) in an organic solvent to self-cyclize with the existence of an oxidant, and performing after-treatment when the reaction is finished to obtain a compound of a formula (4); and S2) reacting the compound of the formula (4) and a compound of a formula (5) in an oxygen atmosphere with the existence of a palladium catalyst, an organic ligand and an acidic compound in a solvent, and performing after-treatment after the reaction is finished to obtain a compound of the formula (6). A plurality of technical characteristics of each step are innovatively optimized in the method, and the brand-new synthetic method and synthetic route for preparing the compounds of this type are provided. The method has a good industrial prospect and good application value.
