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.
Immobilization of a Pd(ii)-containing N-heterocyclic carbene ligand on porous organic polymers: efficient and recyclable catalysts for Suzuki-Miyaura reactions
Gao, Xiyue,Lin, Hongwei,Liu, Cijie,Luo, Qionglin,Ouyang, Yuejun,Xiang, Bailin,Xiang, Dexuan,Yao, Huan,Zhou, Nonglin
, p. 3676 - 3680 (2021/06/17)
Palladium coordinated with N-heterocyclic carbene-functionalized porous organic polymers (Pd@POPs) was successfully preparedviaScholl coupling reaction and a successive immobilization method. The protocol features simple reaction conditions, easy separation, high yield and low cost. The structure and composition of Pd@POPs were characterized by N2sorption, TGA, FT-IR, SEM, EDX, TEM, XPS and ICP. Then the obtained heterogeneous catalysts were applied in Suzuki-Miyaura coupling reaction to evaluate their catalytic performance. The Pd@POPs displayed high catalytic activity for the Suzuki-Miyaura coupling reaction in an EtOH/H2O solvent. A 0.03 mol% Pd loading was sufficient for the reaction with a high turnover number (TON) of 3220. Moreover, the catalyst was easily recovered and reused for at least six consecutive cycles without obvious loss of its initial activity.
Black phosphorus as a metal-free, visible-light-active heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes
Kalay, Erbay,Kü?ükke?eci, Hüseyin,Kilic, Haydar,Metin, ?nder
supporting information, p. 5901 - 5904 (2020/06/04)
Black phosphorus (BP) is for the first time employed as a metal-free, heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes with aryl diazonium salts. The arylated heteroarenes are obtained in moderate to good yields under visible-light illumination, and the protocol is shown to be applicable for the scale-up synthesis.
