100956-66-9

Upstream product

• 4083-64-1 Tosyl isocyanate 
• 866252-52-0 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 709-09-1 3,4-dimethoxynitrobenzene 
• 533934-31-5 N-(3,4-dimethoxyphenyl)-4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 6315-89-5 3,4-dimethoxyaniline 

Downstream Products

• 533934-31-5 N-(3,4-dimethoxyphenyl)-4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 34711-50-7 N-(4,5-dimethoxy-2-nitrophenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Corrigendum to “Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates” [Tetrahedron Lett. 59 (2018) 671–674](S0040403918300352)(10.1016/j.tetlet.2018.01.022)

The authors regret that the structure of Scheme 3 is shown incorrectly. The structure of the compound 3e' is shown correctly here.[Figure presented] The penultimate paragraph of the “Results and Discussion” section should read as follows: During the investigation of several substrates, we observed the unexpected product 3e' which had a diphenyl backbone with a tosyl amine in 45% yield (Scheme 3). This structure was confirmed by 1H NMR, 13C NMR, and high-resolution mass spectroscopy. The diphenyl scaffold is useful to develop new ligands, or synthesize materials, pharmaceuticals, and natural products.The Authors also note corrections needed to the data of compound 3j in the Supplementary Data files. This should be re-written as follows: 13C NMR (125 MHz, CDCl3) δ 150.4 (dd, 1C, JC–F = 242.8, 8.2 Hz), 148.3 (dd, 1C, JC–F = 240.6, 7.3 Hz), 144.4, 135.6, 133.0 (dd, 1C JC–F = 8.1, 3.3 Hz), 129.9, 127.3, 118.1 (q, 1C, JC-F = 3.3 Hz), 117.8 (dd, 1C, JC–F = 18.2, 1.3 Hz), 111.8 (d, 1C, JC–F = 20.3 Hz), 21.6.The updated Supplementary Data files have been published online with this Corrigendum. The authors would like to apologise for any inconvenience caused.

Highly chemo- and regioselective C-P cross-coupling reaction of quinone imine ketals with Ar2P(O)H to construct: Ortho -amino triarylphosphine derivatives

A highly chemo- and regioselective approach for the construction of ortho-amino triarylphosphine oxides has been achieved through a C-P cross-coupling reaction involving quinone imine ketals (QIKs) with Ar2P(O)H and catalyzed via a Lewis base. This alternative protocol provided a wide substrate scope with excellent yields (82-95%), and a variety of ortho-amino triarylphosphines were obtained with high yields (87-95%) via further reductive reaction. Furthermore, this reaction could be scaled-up and several synthetic transformations were accomplished for the construction of functionalized organophosphorus.

Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates

An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor

Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant

Selective oxidative homo- and cross-coupling of electron-rich phenols and anilides was developed using nitrosonium tetrafluoroborate as a catalyst. Oxidative coupling of phenols revealed unusual selectivities, which translated into the unprecedented synthesis of inverse Pummerer-type ketones. Mechanistic studies suggest that oxidative coupling of phenols and anilides shares a common pathway via homolytical heteroatom-hydrogen bond cleavage. Nitrosonium salt catalysis was applied for cross-dehydrogenative coupling initiated by generation of heteroatom-centered radicals.

Electron-withdrawing substituted benzenesulfonamides against the predominant community-associated methicillin-resistant Staphylococcus aureus strain USA300

A small focused chemical library constituted of sulfonamides was synthesized. These compounds were designed to lack the p-aminobenzene moiety typically found in sulfonamide antibiotics. Antimicrobial activities of these synthetic compounds were investigated against global predominant methicillin-resistant Staphylococcus aureus (MRSA) strain USA300 (SF8300) and control strains of Staphylococcus aureus (S. aureus) ATCC 25923 and ATCC 29213 using disk diffusion and microdilution assays. Based on susceptibility results, potent S. aureus and MRSA USA300 growth inhibitors such as N-[3,5- bis(trifluoromethyl)phenyl]-4-bromobenzenesulfonamide with minimum inhibitory concentration (MIC) as low as 5.6 μg/cm3 along with other effective sulfonamides were discovered. Structure-activity correlations revealed that these desamino-benzenesulfonamides required electron-withdrawing substituents to be effective inhibitors of bacterial pathogen growth. In addition, their ability to inhibit growth of S. aureus strains was retained even when bacterial folate synthetic intermediate, p-aminobenzoic acid (PABA), was supplemented, whereas PABA supplementation completely diminished the antibacterial activity of the known sulfa drug tested, sulfamethoxazole. The sulfa-resistant MRSA strain COL also showed great susceptibility to these desamino-benzenesulfonamides. These results imply a unique mechanism of growth inhibition by these potent desamino-benzenesulfonamides, different from the well-known folate pathway target of sulfonamide antibiotics.

Intramolecular reactions of alkynes with furans and electron rich arenes catalyzed by PtCl2: The role of platinum carbenes as intermediates

5-(2-Furyl)-1-alkynes react, with PtCl2 as catalyst, to give phenols. On the basis of DFT calculations, a cyclopropyl platinacarbene complex was found as the key intermediate in the process. The cyclopropane and dihydrofuran rings of this intermediate open to form a carbonyl compound, which reacts with the platinum carbene to form an oxepin, which is in equilibrium with an arene oxide. When the reaction is carried out in the presence of water, dicarbonyl compounds are obtained, which support the proposed mechanism. Other cyclizations of alkynes with furans or electron-rich arenes give products of apparent Friedel-Crafts-type reactions, although these processes could also proceed by pathways involving the formation of cyclopropyl platinum carbenes.