17113-33-6Relevant articles and documents
Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketonest
Kel'in, Alexander V.,Gevorgyan, Vladimir
, p. 95 - 98 (2002)
A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.
Reaction of Aryl Triflates with Heteroaryllithiums via Aryne Intermediates
Reuter, Kelly Hardee,Scott, William J.
, p. 4722 - 4726 (1993)
Unhindered aryl triflates react with a mixture of 1.5 equiv of LDA and 8-10 equiv of 2-lithiofuran at -78 deg C to form 2-arylfurans in 50-60percent yield via the corresponding arynes.Regioisomeric ratios of products are similar to those observed for reactions of arynes with well-precedented nucleophiles, such as metal amides.Steric hindrance ortho to the triflate increases the cine to ipso ratio, but lowers overall yields due to enhanced nucleophilic attack at sulfur leading to formation of the corresponding phenol.Use of 2-lithiothiophene affords the analogous arylthiophene.
Synthesis and structure-activity relationship studies of 3-biaryl-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters
Torun, Lokman,Madras, Bertha K.,Meltzer, Peter C.
, p. 2762 - 2772 (2012)
Stille cross coupling protocols were utilized for the synthesis of 3-(biaryl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl esters, which furnished products in high yields where in some cases Suzuki coupling under the conditions utilized provided complex reaction mixture. Samarium iodide reduction of the resulting coupling products produced both of the 2β-carbomethoxy-3- biaryl-8-oxabicyclo[3.2.1]octane diastereomers and the 2α-carbomethoxy-3- biaryl-8-oxabicyclo[3.2.1]octane diastereomers. Among the series synthesized, the benzothiophene substituted compounds demonstrated significant binding profiles of inhibition of WIN 35,438 with 177-fold selectivity for DAT versus SERT.
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Nishio,Omote
, p. 103 (1976)
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Thermal Rearrangement of Allenyl Ketones
Huntsman, William D.,Yin, Tyze-Kuan
, p. 3813 - 3814 (1983)
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1,2-Carbopentafluorophenylation of Alkynes: The Metallomimetic Pull-Push Reactivity of Tris(pentafluorophenyl)borane
Shibuya, Masatoshi,Matsuda, Miki,Yamamoto, Yoshihiko
supporting information, p. 8822 - 8831 (2021/05/21)
We report the novel single-step 1,2-dicarbofunctionalization of an arylacetylene with an allylsilane and tris(pentafluorophenyl)borane [B(C6F5)3] involving C?C bond formation with C?H bond scission at the β-position to the silicon atom of an allylsilane and B→C migration of a C6F5 group. The 1,2-carbopentafluorophenylation occurs smoothly without the requirement for a catalyst or heating. Mechanistic studies suggest that the metallomimetic “pull-push” reactivity of B(C6F5)3 imparts consecutive electrophilic and nucleophilic characteristics to the benzylic carbon of the arylacetylene. Subsequent photochemical 6π-electrocyclization affords tetrafluoronaphthalenes, which are important in the pharmaceutical and materials sciences. Owing to the unique reactivity of B(C6F5)3, the 1,2-carbopentafluorophenylation using 2-substituted furan proceeded with ring opening, and the reaction using silyl enolates formed a C?C bond with C?O bond scission at the silyloxy-substituted carbon.
Efficient and Economical Preparation of Hypercrosslinked Polymers-palladium Based on Schiff Base as Recyclable Catalyst for Suzuki-Miyaura Reactions
Gao, Xiyue,Lin, Hongwei,Liu, Shasha,Luo, Qionglin,Ouyang, Yuejun,Xiang, Bailin,Xiang, Dexuan,Yao, Huan,Zhang, Li
supporting information, p. 1879 - 1882 (2021/10/29)
A novel hypercrosslinked polymer (HCP) was prepared via Friedel-Crafts alkylation reaction of Schiff base with benzene and formaldehyde dimethyl acetal (FDA) promoted by FeCl3. The HCP was then metalated with Pd(II) to form heterogeneous catalyst. The protocol featured low cost, mild conditions, readily available materials, easy separation and high yield. Physicochemical methods, including IR, N2 sorption, ICP, TGA, XPS, SEM, EDX, and TEM, were used to characterize the catalyst structure and composition. The results reveal that the heterogeneous catalyst possesses high specific surface area, large pore volume, good chemical and thermal stability, and highly dispersed palladium. The heterogeneous catalysts were applied in Suzuki-Miyaura coupling reaction to evaluate their catalytic performance. The experiments reflected that the HCPs-Pd(OAc)2 was an efficient catalyst for Suzuki-Miyaura reactions with the yield of biaryl up to 99%, while the TON could reach 2250. The reusability test showed the catalyst was easily recovered and reused for at least six times without obvious decrease in activity.
Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex
Paul, Swagata,Das, Kanak Kanti,Manna, Samir,Panda, Santanu
supporting information, p. 1922 - 1927 (2020/02/04)
The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.
