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.
Aryl Coupling through Borate Complexes with Ethanolamine.
Pelter, Andrew,Williamson, Hugh,Davies, Gareth M.
, p. 453 - 456 (1984)
The scope and limitations of aromatic coupling by the action of N-bromsuccinimide on stable diarylethanolamine borate salts are disclosed.The procedure is an excellent, regiospecific procedure for the coupling of furyl and thienyl residues to each other or to aromatic rings in mild conditions and without scrambling.
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.
Phosphine-free Suzuki cross-coupling reactions under ultrasound
Silva, Aires da Concei??o,de Souza, Andréa Luzia F.,Antunes
, p. 3104 - 3107 (2007)
Suzuki cross-coupling reaction was successfully carried out in ethylene glycol under phosphine-free conditions to obtention of biaryls using ultrasonic irradiation. High yields were obtained using different palladium and bases sources. The catalyst was recycled up to three times with good to moderate activity.
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.
Palladium nanoparticles deposited on a graphene–benzimidazole support as an efficient and recyclable catalyst for aqueous-phase Suzuki–Miyaura coupling reaction
Sarvestani, Mosayeb,Azadi, Roya
, (2017)
Graphene oxide was functionalized with benzimidazole for palladium immobilization. The resultant graphene–benzimidazole-supported palladium composite (G-BI-Pd) was characterized using infrared and Raman spectroscopies, transmission electron microscopy and
Microwave- and ultrasound-assisted Suzuki-Miyaura cross-coupling reactions catalyzed by Pd/PVP
de Souza, Andréa Luzia F.,da Silva, Lucyane C.,Oliveira, Bianca L.,Antunes
, p. 3895 - 3898 (2008)
Suzuki-Miyaura reactions using Pd/PVP as a catalyst source were carried out in water-ethanol solution. Under MW, sonication or thermal condition yields were very similar, from moderate to very good, in a variety of examples. However, TOFs were very different, 750/h under MW, 250/h under sonication, and 28/h under thermal conditions. Studies carried out under sonication showed that the whole system after product extraction can be re-used at least twice without any noticeable loss of yield.
Quaternary Ammonium Periodate as a New Oxidizing Agent
Inomata, Katsuhiko,Nakayama, Yukiharu,Kotake, Hiroshi
, p. 565 - 566 (1980)
Quaternary ammonium periodate has been found to be a useful oxidizing agent to convert a 1,2-diol and an olefin to the corresponding carbonyl compound in anhydrous aprotic solvents.The resulting carbonyl compounds have been reacted with alkyllithium to prepare alcohols in one-pot from a 1,2-diol or an olefin.
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.
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.
