7515-27-7Relevant academic research and scientific papers
Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions
Xiao, Guorong,Wu, Kaifu,Zhou, Wei,Cai, Qian
supporting information, p. 4988 - 4991 (2021/10/14)
A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).
Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues
Hai, Li,Lai, Ruizhi,Lv, Shan,Nie, Ruifang,Wu, Yong,Yang, Zhongzhen,chen, Kang
, (2022/02/03)
A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw
Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids
Ghosh, Subhankar,Ghosh, Rajat,Chattopadhyay, Shital K.
, (2020/09/15)
A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-
Visible light induced 3-position-selective addition of arylpropiolic acids with ethersviaC(sp3)-H functionalization
Luo, Jun,Wan, Zi-Juan,Yuan, Xiao-Feng
supporting information, p. 3258 - 3262 (2020/05/14)
Although the 2-position-selective decarboxylative coupling or addition of arylpropiolic acids with cyclic ethers has been intensively investigated, selective functionalization of arylpropiolic acids at the 3-position is still a big challenge. Herein, an i
A Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids
Zhang, Hua,Zhang, Guo-Min,He, Shuai,Shi, Zhi-Chuan,Zhang, Xiao-Mei,Wang, Ji-Yu
supporting information, p. 8337 - 8344 (2020/11/03)
An iron-catalyzed cascade reaction of radical reduction of allyl alcohols and acetylenic acids to construct polysubstituted α-alkenyl lactones has been developed. In this paper, various allyl alcohols can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramolecular reflex-Michael addition. In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a β-methylene tetrahydrofuran and tetrahydrofuran diene.
NiCl2-catalyzed radical cross decarboxylative coupling between arylpropiolic acids and cyclic ethers
Wan, Zi-juan,Wang, Jin-yuan,Luo, Jun
supporting information, p. 613 - 616 (2019/01/29)
A direct alkenylation of cyclic ethers via radical cross decarboxylative coupling process catalyzed by NiCl2 and using DTBP as radical initiator and oxidant was developed. A variety of arylpropiolic acids and cyclic ethers were transformed into the corresponding 2-arylvinyl cyclic ethers in moderate to excellent yields. Mechanistic experiments were conducted to determine the nature of the reaction intermediates, and a plausible reaction mechanism involving NiCl2-promoted radical process was proposed.
Visible Light-Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis
Yang, Liangfeng,Li, Haifeng,Du, Yijun,Cheng, Kai,Qi, Chenze
, p. 5030 - 5041 (2019/11/03)
A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely-functionalized aryl alkynes could be synthesized under mild, neutral and transition metal-free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal-free operation, another key point of this method is that the organic dye catalyst acts as an excited-state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination. (Figure presented.).
Method for synthesizing alpha-alkynyl substituted ether compounds
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Paragraph 0037; 0039, (2018/04/01)
The invention discloses a method for preparing alpha-alkynyl substituted ether compounds. The method comprises the following steps: taking propiolic acid as a raw material, and synthesizing substituted phenylpropiolic acid under conditions of substituted iodobenzene, 1,8-diazabicyclo[5.4.0]undec-7-ene, (beta-4)-platinu and dimethyl sulfoxide; taking substituted phenylpropiolic acid and p-bromophenol as raw materials, and synthesizing p-bromophenyl substituted phenylpropiolic acid ester under the conditions of 4-dimethylaminopyridine and N,N'-Dicyclohexylcarbodiimide; and performing an alkynylation reaction on the p-bromophenyl substituted phenylpropiolic acid ester in participation of tert-butyl hydroperoxide, cesium carbonate and tetrahydrofuran, and finally synthesizing alpha-alkynyl substituted ether products. According to the method disclosed by the invention, simple and readily available acetylene esters serve as an alkynylation reagent, and the target products, namely alpha-alkynyl substituted ether compounds, are synthesized in a green and environmental-friendly manner under mild conditions. The compounds play an important role in construction of multiple medical intermediates and bio-active structures.
Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents
Cui, Fei-Hu,Chen, Jing,Mo, Zu-Yu,Su, Shi-Xia,Chen, Yan-Yan,Ma, Xian-Li,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming,Xu, Yan-Li
supporting information, p. 925 - 929 (2018/02/22)
A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.
Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
, p. 1218 - 1231 (2018/02/16)
Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
