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Journal of Organic Chemistry
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#1Kingshuk MahantyH-Index: 1
#2Debabrata MaitiH-Index: 37
Last.Suman De SarkarH-Index: 18
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This study reveals a transition metal and external oxidant free electrochemical method for the C3–H sulfonylation of bio-logically diverse 2H-indazoles at room temperature and under ambient air. Using various sulfonyl hydrazides as the sulfonyl precursor, a series of sulfonylated indazole derivatives containing a broad spectrum of functional groups were synthesized up to 92% yield. Mechanistic studies suggest a precedented radical pathway is operating in the electrochemical pro-cess.
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#1Abdur RahimH-Index: 1
#2Biswajit SahariahH-Index: 1
Last.Bani Kanta SarmaH-Index: 11
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We report the solid-phase synthesis of N,Nʹ-di(acylamino)-2,5-diketopiperazine (daa-DKP), an acylhydrazide-based conformationally rigid 2,5-DKP scaffold having exocyclic N-N bonds. We also show that different combinations of acylhydrazides, carbazates, semicarbazides, amino acids and primary amines can be used to synthesize highly diverse collection of hybrid DKP molecules via the solid-phase submonomer synthesis route. Finally, we show incorporation of a methyl substituent in one of the carbon ...
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A selective and large-scale synthesis of [8]cycloparaphenylene (CPP) was achieved in seven steps starting from commercially available 4-bromo-4’-hydroxybiphenyl and 4,4’-dibromobiphenyl. The key unsymmetrical tetraring unit, 4-bromophenyl and 4’-bromobiphenyl-substituted cis-1,4-bis(triethylsiloxy)-2,5-cyclohexadiene-1,4-diyl (5fA), was synthesized on an ~50 g scale by stereoselective cis-addition of 4-bromo-4’-lithiobiphenyl to 4-(4-bromophenyl)-4-hydroxy-2,5-cyclohexadien-1-one, which was synt...
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We applied a multicomponent approach to access a library of densely functionalized homo- and hetero-multivalent glycomimetics comprising aldehyde, amine and isocyanide components related to isopropylidene-protected D-fructose, L-sorbose, D-galactose and D-allose. Passerini products were obtained in very good yields (up to 78 %) and high diastereoselectivities (up to 98:2). Three types of products were obtained by the Ugi reaction; along with the “classical” four-component product - α-acylaminoam...
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A method for the three-component cycloaddition of enoates, alkynes, and aldehydes has been developed. Building upon previous work by this group in which stoichiometrically generated metallacycles undergo alkylation, we report a catalytic, alkylative [3+2] cycloaddition. From simple starting materials, structurally complex cyclopentenones may be rapidly assembled. Computational investigation of the mechanism (ωB97X-D3/cc-pVTZ // ωB97X/6-31G(d)) identified three energetically feasible pathways. Ba...
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#1Yota Suzuki (Waseda University)H-Index: 2
#2Daisuke Kusuyama (Waseda University)
Last.Koji Ishihara (Waseda University)H-Index: 18
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Fundamental information on the reactivities of boronic acids toward catechols in aqueous solution is required in all the fields dealing with boronic acid. However, comprehensive studies on reactivity are often hindered by so-called “proton ambiguity,” which makes it impossible for the rate constants of boronic acid and boronate ion to be determined separately. Herein, we set up two reaction systems without proton ambiguity: (1) Alizarin Red S and (2) Tiron with several boronic acids (RB(OH)2) wi...
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A short step total synthesis of karrikinolide has been achieved. The both α and α’ positions of O-acylated acetol were alkylated by the boron-mediated aldol type acetal addition reaction. One pot sequence including the Arbuzov reaction, intramolecular Horner-Wadsworth-Emmons reaction, acidic hydrolysis of acetals, and pyran formation provided karrikinolide. This procedure was applicable to gram-scale synthesis of karrikinolide.
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#1Hanghang WangH-Index: 1
#2Yanwei ZhaoH-Index: 6
Last.Xiaobing WanH-Index: 19
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A simple and efficient method has been developed for the preparation of primary oxamates and α-ketoamides through the oxidative coupling of diazo compounds and NH4I. Under the optimized reaction conditions, a range of diazo esters and α-diazoketones was explored, and the corresponding products were obtained in moderate to good yields. This protocol fea-tures metal free, mild conditions, wide substrate scopes and operational simplicity.
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#2Yi FangH-Index: 6
Last.Shun-Jun JiH-Index: 44
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A new practical synthesis of 2-amino-1,3-selenazole with transition-metal-free multicomponent reaction was reported here. A series of 2-amino-1,3-selenazole derivatives were afforded by the nucleophilic addition of amines to an isoselenocyanate formed in situ, followed by a Michael addition reaction and aromatization. The products were isolated from moderate to excellent yields.
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#1Hua WangH-Index: 15
#2Jie LiuH-Index: 5
Last.Yan-Biao KangH-Index: 18
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An organocatalyzed aerobic benzylic C-H oxidation of alkyl- and aryl heterocycles has been developed. This transition metal-free method is able to overcome the electron-withdrawing effect as well as product-inhibition effects in heterobenzylic radical oxidation. A variety of ketones bearing N-heterocyclic groups could be prepared under relatively mild conditions with moderate to high yields.
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