- Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – A powerful hypervalent iodine(V) oxidant
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The selective preparation of 2-iodoxybenzenesulfonic acid (IBS, as potassium or sodium salts) by oxidation of sodium 2-iodoben-zenesulfonate with Oxone or sodium periodate in water is reported. The single crystal X-ray diffraction analysis reveals a compl
- Mironova, Irina A.,Postnikov, Pavel S.,Yusubova, Rosa Y.,Yoshimura, Akira,Wirth, Thomas,Zhdankin, Viktor V.,Nemykin, Victor N.,Yusubov, Mekhman S.
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- Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
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Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.
- Bourbon, Paul,Appert, Emeline,Martin-Mingot, Agnès,Michelet, Bastien,Thibaudeau, Sébastien
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supporting information
p. 4115 - 4120
(2021/06/21)
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- Functionalization of α-C(sp3)?H Bonds in Amides Using Radical Translocating Arylating Groups
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α-C?H arylation of N-alkylamides using 2-iodoarylsulfonyl radical translocating arylating (RTA) groups is reported. The method allows the construction of α-quaternary carbon centers in amides. Various mono- and disubstituted RTA-groups are applied to the arylation of primary, secondary, and tertiary α-C(sp3)?H-bonds. These radical transformations proceed in good to excellent yields and the cascades comprise a 1,6-hydrogen atom transfer, followed by a 1,4-aryl migration with subsequent SO2 extrusion.
- Radhoff, Niklas,Studer, Armido
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supporting information
p. 3561 - 3565
(2021/01/04)
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- Switchable Divergent Synthesis in Gold-Catalyzed Difunctionalizations of o-Alkynylbenzenesulfonamides with Aryldiazonium Salts
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Gold-catalyzed difunctionalizations of o-alkynylbenzenesulfonamides with aryldiazonium salts are reported herein. Upon irradiation with the blue LEDs, benzosultam products were formed via aminoarylation accompanied by the release of N2. Without irradiatio
- Li, Jun,Shi, Hongwei,Zhang, Shan,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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supporting information
p. 7713 - 7717
(2021/10/20)
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- One-pot, Pd/Cu-catalysed synthesis of alkynyl-substituted 3-ylidene-dihydrobenzo[d]isothiazole 1,1-dioxides
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Enyne-substituted benzoisothiazole derivatives have been synthesised under one-pot, operationally simple conditions using 2-iodo-N-(trimethylsilylethynyl)benzenesulfonamides and terminal alkynes as starting materials and a palladium–copper-based catalytic system. The structure of these heterocycles has been demonstrated by NMR spectroscopy and confirmed by X-ray crystallographic analysis. A plausible reaction mechanism has been proposed.
- Etsè, Koffi Sénam,Dassonneville, Benjamin,Zaragoza, Guillermo,Demonceau, Albert
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supporting information
p. 789 - 793
(2017/03/31)
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- Design, synthesis and biological evaluation of benzo[1.3.2]dithiazolium ylide 1,1-dioxide derivatives as potential dual cyclooxygenase-2/5-lipoxygenase inhibitors
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3-(4-Bromophenyl)-6-nitrobenzo[1.3.2]dithiazolium ylide 1,1-dioxide (5) was discovered as a new prototype for dual inhibitors of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX). Thus, the structure-activity relationships of benzo[1.3.2]dithiazolium ylide 1,1-dioxide skeleton were carried out. The 6-NO2 group played an essential role in the inhibitory activity. In addition, moderate-sized lipophilic substituents at the para-position of the 3-aryl moiety were required for dual COX-2/5-LOX inhibitory activity. Among the identified potent dual inhibitors, 3-(4-tbutylphenyl) derivative 30c (IC50 values of 0.27 μM and 0.30 μM against COX-2 and 5-LOX, respectively) and 3-(4-biphenyl) derivative 30f (IC50 values of 0.50 μMand 0.15 μMagainst COX-2 and 5-LOX, respectively) were the most potent dual COX-2/ 5-LOX inhibitors. Intraperitoneal administration of 30c at 100 mg/kg demonstrated potent acute antiinflammatory activity. As a result, benzo[1.3.2]dithiazolium ylide 1,1-dioxide represented a novel scaffold for the exploitation in developing dual COX-2/5-LOX inhibitors.
- Tan, Chen-Ming,Chen, Grace Shiahuy,Chen, Chien-Shu,Chang, Pei-Teh,Chern, Ji-Wang
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experimental part
p. 6316 - 6328
(2011/12/02)
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- Preparation and X-ray structures of 2-[(aryl)iodonio]benzenesulfonates: novel diaryliodonium betaines
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Herein we present a concise preparation and characterization of 2-[(aryl)iodonio]benzenesulfonates. Determination of the X-ray crystal structure reveals a distorted trigonal bipyramidal molecular geometry about iodine and a pseudo-square geometry within t
- Justik, Michael W.,Protasiewicz, John D.,Updegraff, James B.
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supporting information; experimental part
p. 6072 - 6075
(2010/03/01)
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- Synthesis and biological evaluation of linear phenylethynylbenzenesulfonamide regioisomers as cyclooxygenase-1/-2 (COX-1/-2) inhibitors
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A group of regioisomeric phenylethynylbenzenesulfonamides possessing a COX-2 SO2NH2 pharmacophore at the para-, meta- or ortho-position of the C-1 phenyl ring, in conjunction with a C-2 substituted-phenyl (H, OMe, OH, Me, F) group, w
- Anana, Raymond,Rao, P.N. Praveen,Chen, Qiao-Hong,Knaus, Edward E.
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p. 5259 - 5265
(2007/10/03)
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