189099-57-8Relevant articles and documents
Photoinduced copper-catalyzed site-selective C(sp2)-C(sp) cross-coupling via aryl sulfonium salts
Liang, Lei,Niu, Hong-Ying,Li, Ren-Long,Wang, Yao-Fei,Yan, Jin-Kai,Li, Chang-Gong,Guo, Hai-Ming
, p. 6842 - 6846 (2020)
The classical Sonogashira reaction of aryl electrophiles in the presence of Pd catalysts has been well established as a potent method for arylalkyne synthesis. However, the site-selective C(sp2)-C(sp) cross-coupling strategy using a non-noble-metal catalyst is rare. An efficient alternative approach for the synthesis of arylalkynes via a Cu-catalyzed Sonogashira-type reaction promoted by visible light is described. This method enables site-selective alkynylation from aryl sulfonium salts derived from diverse arenes to a set of arylalkynes with high selectivity and high functional-group compatibility. Moreover, rapid alkynylation of drug molecules is demonstrated.
Method for preparing aryl internal alkyne compound through light-mediated copper catalysis
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Paragraph 0031-0033; 0037-0039, (2020/09/09)
The invention relates to a method for preparing an aryl internal alkyne compound through light-mediated copper catalysis, and belongs to the field of organic chemistry. An aryl sulfide salt and a terminal alkyne are used as raw materials, a + 1 valent copper salt is used as a catalyst, potassium carbonate is used as alkali, reaction is performed in solvents such as DMSO to obtain the aryl internalalkyne compound, and the yield is 50%-86%. According to the synthetic method, the raw materials are easy to obtain, the reaction conditions are mild, a simple, convenient, green and efficient synthetic route of the internal alkyne compound is provided, and an effective method for introducing alkynyl into aromatic ring-containing drug molecules is provided.
Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes
Weingand, Vanessa,Wurm, Thomas,Vethacke, Vanessa,Dietl, Martin C.,Ehjeij, Daniel,Rudolph, Matthias,Rominger, Frank,Xie, Jin,Hashmi, A. Stephen K.
supporting information, p. 3725 - 3728 (2018/02/23)
Push–pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.
Palladium-Catalyzed Decarboxylative Coupling Reactions of Propiolic Acid Derivatives and Arylsulfonyl Hydrazide
Park, Jaerim,Song, Kwang Ho,Lee, Sunwoo
, p. 3197 - 3204 (2018/08/12)
Arylsulfonyl hydrazides were employed as coupling partners for the decarboxylative coupling reaction of propiolic acid derivatives. When the reaction was conducted using Pd(TFA) 2 (1.0 mol%), dppp (1.0 mol%), and Cu(OAc) 2 (2.4 equiv
New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer
Witzel, Sina,Sekine, Kohei,Rudolph, Matthias,Hashmi, A. Stephen K.
supporting information, p. 13802 - 13804 (2018/12/14)
The scope of photosensitizer-free visible light-driven gold-catalyzed cross-coupling was evaluated by a wide variety of organoboron and organosilicon species using four equivalents of aryldiazonium salts and (4-CF3-C6H4)3PAuCl in MeOH. In addition, a C(sp or sp2)-C(sp2) cross-coupling of organotrimethylsilanes and aryldiazonium salts was investigated. The reactions can be conducted under very mild reaction conditions, with a reduced amount of aryldiazonium salt (1.2 equiv.) by using a catalytic amount of Ph3PAuNTf2 in MeCN under irradiation with blue LEDs at room temperature.
Alkyne compound and synthesis method and application thereof
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Paragraph 0067-0069, (2018/12/13)
The invention relates to the field of organic synthesis, in particular to an alkyne compound and a synthesis method and application thereof. The invention discloses a method for synthesizing an alkynecompound, which comprises the following steps: allowing a compound in formula (II) and a compound in formula (III) to react in the presence of an inert solvent under the action of catalyst and oxidizing agent to obtain a compound in formula (I). The synthesis method has simple and easily available materials, safe and simple operation, wide application range of substrate and good selectivity, doesn't need pre-activating, and is easily involved in free radical reaction, and byproducts are nitrogen and water, which conforms to sustainable green chemistry. The alkyne compound obtained by the above synthesis method is a brand-new alkyne compound, and the alkyne compound can be widely used in the fields of medicine and materials, and solves the technical problems of high cost, low stability andcomplication of alkyne compound synthesis reaction in the prior art.
Hydrazone–Cu-Catalyzed Suzuki–Miyaura-Type Reactions of Dibromoalkenes with Arylboronic Acids
Watanabe, Kohei,Mino, Takashi,Hatta, Chikako,Ishikawa, Eri,Yoshida, Yasushi,Sakamoto, Masami
, p. 3612 - 3619 (2017/07/22)
We have found that Suzuki–Miyaura-type reactions of dibromoalkenes with arylboronic acids using a hydrazone–Cu catalyst system proceeded smoothly under mild conditions to afford the corresponding internal alkyne derivatives in good yields. Furthermore, we also succeeded in the synthesis of o-allyloxy(ethynyl)benzene derivatives, which are known to be effective precursors of various heterocyclic compounds, through this reaction.
Palladium-Catalyzed Desulfitative Cross-Coupling of Arylsulfonyl Hydrazides with Terminal Alkynes: A General Approach toward Functionalized Internal Alkynes
Qian, Liang-Wei,Sun, Mengli,Dong, Jianyu,Xu, Qing,Zhou, Yongbo,Yin, Shuang-Feng
, p. 6764 - 6769 (2017/07/15)
A palladium-catalyzed Sonogashira-type coupling between arylsulfonyl hydrazides and terminal alkynes via Ar(C)-S bond cleavage is disclosed, which enables the general synthesis of functionalized internal alkynes, especially the Br-substituted ones, in good to excellent yields under acid- and base-free conditions.
Sonogashira reaction using arylsulfonium salts as cross-coupling partners
Tian, Ze-Yu,Wang, Shi-Meng,Jia, Su-Jiao,Song, Hai-Xia,Zhang, Cheng-Pan
, p. 5454 - 5457 (2017/11/06)
Triarylsulfonium, alkyl- and fluoroalkyl(diaryl)-sulfonium, and aryl(dialkyl)sulfonium triflates are successfully used as a new family of cross-coupling participants in the Sonogashira reaction as aryldiazonium, diaryliodonium, and tetraphenylphosphonium salts. It was found that terminal alkynes reacted mildly with triarylsulfonium or (2,2,2-trifluoroethyl)diphenylsulfonium triflate at room temperature under Pdand Cu-cocatalysis to give the corresponding arylalkynes in up to >99% yield. This protocol represents the first use of arylsulfonium salts as cross-coupling partners in the Pd/Cu-catalyzed Sonogashira reaction.
Rapid access to unsymmetrical tolanes and alkynones by sequentially palladium-catalyzed one-pot processes
G?tzinger, Alissa C.,Müller, Thomas. J. J.
, p. 3498 - 3500 (2016/04/19)
Alkynones as well as unsymmetrically substituted tolanes (diarylalkynes) can be rapidly generated in a one-pot fashion via sequential palladium catalysis. Terminal alkynes, formed in situ by protecting-group free palladium-catalyzed coupling of aryl iodides with ethynyl magnesium bromide, are subsequently transformed by Sonogashira coupling with aryl halides or aroyl chlorides to furnish unsymmetrically substituted alkynes in good to excellent yields.
