734-18-9Relevant academic research and scientific papers
Preparation method of alpha, alpha-difluoro-beta-ketone sulfone compound
-
Paragraph 0109; 0114-0117, (2021/01/28)
The invention provides a preparation method of an alpha, alpha-difluoro-beta ketone sulfone compound, and belongs to the technical field of chemistry. The invention firstly provides a composition forpreparing a compound shown as a formula I, which consists of the following components: a compound 1, a fluoride initiator and an organic solvent; Ar1 and Ar2 are independently selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroatom aryl group respectively. The invention also provides a method for preparing alpha, alpha-difluoro-beta-ketone sulfone compounds from the composition. According to the invention, metal fluoride is used as an initiator, and a series of compounds can be prepared under mild conditions. The preparation method is simple in synthetic route, good in yield and high in purity; the method has the advantages of excellent functional group adaptability and the like, can be used for preparing alpha, alpha-difluoro-beta-ketone sulfone compounds with various functional groups, and is successfully applied to later modification of natural products and drug molecules. Besides, the reaction scale of the method can be amplified to gram level, and the method can be used for industrial amplification production and has a good application prospect.
Catalytic AgF-Initiated Intramolecular 1,3-Sulfonyl Migration of gem-Difluorovinyl Sulfonates to α,α-Difluoro-β-ketosulfones
Chen, Lei,Li, Xiong,Li, Yue,Lian, Zhong,Sun, Haotian,Xiong, Baojian,Xu, Jie
, p. 9263 - 9268 (2020/11/30)
A 1,3-sulfonyl migration of difluorovinyl sulfonates initiated by a catalytic amount of silver fluoride is presented. α,α-Difluoro-β-ketosulfones were successfully prepared in excellent yields. This method features high chemoselectivity, good functional group tolerance, high atom economy, and mild, environmentally benign reaction conditions. Furthermore, mechanistic experiments indicate that this migration proceeds in an intermolecular pathway and the corresponding sulfinates are possible intermediates.
Photoredox-catalyzed sulfonylation of difluoroenoxysilanes with the insertion of sulfur dioxide
He, Fu-Sheng,Wu, Jie,Xie, Wenlin,Yao, Yanfang
supporting information, p. 9469 - 9472 (2020/09/07)
A photoredox-catalyzed three-component reaction of aryldiazonium tetrafluoroborates with sodium metabisulfite and 2,2-difluoro enol silyl ethers is described. By using sodium metabisulfite as the source of sulfur dioxide, this method provides an elegant a
Synthesis method of alpha, alpha-difluoro-beta-carbonyl sulfone compound
-
Paragraph 0007; 0030-0033, (2020/07/02)
The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of an alpha, alpha-difluoro-beta-carbonyl sulfone compound. The method comprises the following steps: with acetonitrile as a solvent, carrying out a reaction on aryl diazonium salt, sodium metabisulfite and 2,2-difluoroenol silyl ether with Ru(bpy)3Cl2.6H2O being a photosensitizer under blue light irradiation to obtain the 2, 2-difluoroenol silyl ether photosensitizer, thereby generating aryl sulfonyl free radicals from aryl diazonium salt and sodium pyrosulfite under the action of blue light and a photosensitizer, performing addition reaction on 2,2-difluoroenol silyl ether to obtain a free radical intermediate, and performing single-electron oxidation on the free radical intermediate and an excited photosensitizer to obtain the alpha, alpha-difluoro-beta-carbonyl sulfone compound. The synthesis method of the compound has the advantages that with the aryl diazonium salt,sodium metabisulfite and 2,2-difluoroenol silyl ether, which are easy to obtain, being raw materials, strict reaction conditions such as strong base and ultralow temperature are not needed, so that the method has the advantages of strong functional group compatibility, wide substrate application range and the like, a series of alpha, alpha-difluoro-beta-carbonyl sulfone compounds can be efficiently synthesized, and the method has good academic guidance significance and industrial application value.
Stereoselective [3+2] cycloaddition of N-tert-butanesulfinyl imines to arynes facilitated by a removable PhSO2CF2 group: Synthesis and transformation of cyclic sulfoximines
Ye, Wenchao,Zhang, Laijun,Ni, Chuanfa,Rong, Jian,Hu, Jinbo
supporting information, p. 10596 - 10599 (2014/10/15)
An unprecedented [3+2] cycloaddition between N-tert-butanesulfinyl imines and arynes provides a stereoselective method for the synthesis of cyclic sulfoximines. Not only does the difluoro(phenylsulfonyl)methyl group play an important role in facilitating the cycloaddition reaction, it can also be removed or substituted through the transformation of the difluorinated cyclic sulfoximines to cyclic sulfinamides. This journal is the Partner Organisations 2014.
Mono and difluorination of centers α to sulfonates and phosphonates using AcOF
Vints, Inna,Gatenyo, Julia,Rozen, Shlomo
, p. 66 - 69 (2013/03/29)
Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH2SO2 or COCH2PO react with bases to create the corresponding anions wh
An efficient fluorination of β-ketosulfones promoted by a room-temperature ionic liquid at ambient conditions under ultrasound irradiation using Selectfluor F-TEDA-BF4
Heravi, Mohammad Reza Poor
, p. 1399 - 1402 (2011/10/08)
The fluorination reaction involving a β-ketosulfones by Selectfluor was efficiently promoted by the ionic liquid, [Hbim]BF4 (IL) as a reaction medium with methanol as co-solvent at room temperature under ultrasonic irradiation to afford the corresponding mono and difluoro-β-ketosulfones in excellent yields. The advantages of this method include among others the use of a recyclable, non-volatile ionic liquid, which promotes this protocol under room temperature without the requirement of any added catalyst under ultrasonic irradiation.
Synthesis of fluorinated β-ketosulfones and gem-disulfones by nucleophilic fluoroalkylation of esters and sulfinates with di- and monofluoromethyl sulfones
Ni, Chuanfa,Zhang, Laijun,Hu, Jinbo
supporting information; experimental part, p. 3767 - 3771 (2009/09/30)
(Chemical Equation Presented) An efficient and practically useful method for the preparation of α-functionalized mono- and difluoro(phenylsulfonyl) methanes by using a nucleophilic fluoroalkylation methodology was developed. α,α-Difluoro-β-ketosulfones, α
α-Fluorination of β-ketosulfones by Selectfluor F-TEDA-BF4
Loghmani-Khouzani, Hossein,Poorheravi, Mohammad R.,Sadeghi, Majid M.M.,Caggiano, Lorenzo,Jackson, Richard F.W.
, p. 7419 - 7425 (2008/12/20)
Attempted fluorination of β-ketosulfides using Selectfluor resulted only in the isolation of the corresponding diaryl disulfides, presumed to arise by decomposition of an unstable fluorinated intermediate. However, fluorination of β-ketosulfones using Selectfluor under anhydrous conditions does allow the isolation of both mono-and difluorinated products in moderate to good yields.
α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms
Toyota, Akemi,Ono, Yoshinori,Chiba, Jun,Sugihara, Takumichi,Kaneko, Chikara
, p. 703 - 708 (2007/10/03)
Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.
