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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Switching between mono and doubly reduced odd alternant hydrocarbon: designing a redox catalyst
Ahmed, Jasimuddin,Datta, Paramita,Das, Arpan,Jomy, Stephy,Mandal, Swadhin K.
, p. 3039 - 3049 (2021/03/14)
Since the early Hückel molecular orbital (HMO) calculations in 1950, it has been well known that the odd alternant hydrocarbon (OAH), the phenalenyl (PLY) system, can exist in three redox states: closed shell cation (12π e?), mono-reduced open shell neutral radical (13π e?) and doubly reduced closed shell anion (14π e?). Switching from one redox state of PLY to another leads to a slight structural change owing to its low energy of disproportionation making the electron addition or removal process facile. To date, mono-reduced PLY based radicals have been extensively studied. However, the reactivity and application of doubly reduced PLY species have not been explored so far. In this work, we report the synthesis of the doubly reduced PLY species (14π e?) and its application towards the development of redox catalysisviaswitching with the mono-reduced form (13π e?) for aryl halide activation and functionalization under transition metal free conditions without any external stimuli such as heat, light or cathodic current supply.
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.
Palladium supported on triazolyl-functionalized hypercrosslinked polymers as a recyclable catalyst for Suzuki-Miyaura coupling reactions
Lin, Hongwei,Liu, Cijie,Liu, Shasha,Luo, Qionglin,Ouyang, Yuejun,Shu, You,Xiang, Dexuan,Xu, Wei,Zheng, Lijuan
, p. 17123 - 17128 (2020/05/18)
A novel hypercrosslinked polymers-palladium (HCPs-Pd) catalyst was successfully preparedviathe external cross-linking reactions of substituted 1,2,3-triazoles with benzene and formaldehyde dimethyl acetal. The preparation of HCPs-Pd has the advantages of low cost, mild conditions, simple procedure, easy separation and high yield. The catalyst structure and composition were characterized by N2sorption, TGA, FT-IR, SEM, EDX, TEM, XPS and ICP-AES. The HCPs were found to possess high specific surface area, large micropore volume, chemical and thermal stability, low skeletal bone density and good dispersion for palladium chloride. The catalytic performance of HCPs-Pd was evaluated in Suzuki-Miyaura coupling reactions. The results show that HCPs-Pd is a highly active catalyst for the Suzuki-Miyaura coupling reaction in H2O/EtOH solvent with TON numbers up to 1.66 × 104. The yield of biaryls reached 99%. In this reaction, the catalyst was easily recovered and reused six times without a significant decrease in activity.
