7051-15-2Relevant academic research and scientific papers
Derivatives of m-Guaiacol, Their Preparation and Their Uses
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Paragraph 0125; 0136, (2021/11/05)
The invention concerns derivatives of m-guaiacol, their preparation and their uses as biocides, in particular as antibacterials or disinfectants.
Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions
Fu, Zhengjiang,Li, Zhaojie,Song, Yuanyuan,Yang, Ruchun,Liu, Yanzhu,Cai, Hu
, p. 2794 - 2803 (2016/04/26)
Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.
Photocatalytic activation of N-chloro compounds for the chlorination of arenes
Hering, Thea,K?nig, Burkhard
, p. 7821 - 7825 (2016/11/16)
Photoredox catalysis activates N-chloramines and N-chloro-succinimide (NCS) for the electrophilic chlorination of arenes. The photooxidation of the nitrogen atom to a radical cation induces a positive polarization on the chlorine atom, which results in a higher reactivity in electrophilic aromatic chlorination reactions.
Halogenase-Inspired Oxidative Chlorination Using Flavin Photocatalysis
Hering, Thea,Mühldorf, Bernd,Wolf, Robert,K?nig, Burkhard
supporting information, p. 5342 - 5345 (2016/04/26)
Chlorine gas or electropositive chlorine reagents are used to prepare chlorinated aromatic compounds, which are found in pharmaceuticals, agrochemicals, and polymers, and serve as synthetic precursors for metal-catalyzed cross-couplings. Nature chlorinates with chloride anions, FAD-dependent halogenases, and O2 as the oxidant. A photocatalytic oxidative chlorination is described based on the organic dye riboflavin tetraacetate mimicking the enzymatic process. The chemical process allows within the suitable arene redox potential window a broader substrate scope compared to the specific activation in the enzymatic binding pocket. Chlorination of arenes with chloride anions: The photochemical analogue of the enzymatic chlorination of Flavin-adenine dinucleotide (FAD)-dependent halogenases is possible in the presence of riboflavin, air, acetic acid, and blue light (see scheme; RFT=riboflavin tetraacetate).
Halogenated volatiles from the fungus Geniculosporium and the actinomycete Streptomyces chartreusis
Wang, Tao,Rabe, Patrick,Citron, Christian A.,Dickschat, Jeroen S.
supporting information, p. 2767 - 2777 (2014/01/06)
Two unidentified chlorinated volatiles X and Y were detected in headspace extracts of the fungus Geniculosporium. Their mass spectra pointed to the structures of a chlorodimethoxybenzene for X and a dichlorodimethoxybenzene for Y. The mass spectra of some constitutional isomers for X and Y were included in our databases and proved to be very similar, thus preventing a full structural assignment. For unambiguous structure elucidation all possible constitutional isomers for X and Y were obtained by synthesis or from commercial suppliers. Comparison of mass spectra and GC retention times rigorously established the structures of the two chlorinated volatiles. Chlorinated volatiles are not very widespread, but brominated or even iodinated volatiles are even more rare. Surprisingly, headspace extracts from Streptomyces chartreusis contained methyl 2-iodobenzoate, a new natural product that adds to the small family of iodinated natural products.
Pd(II)-catalyzed bromo- and chlorodecarboxylation of electron-rich arenecarboxylic acids
Peng, Xuefeng,Shao, Xiang-Feng,Liu, Zhong-Quan
supporting information, p. 3079 - 3081 (2013/07/11)
A bromo- and chlorodecarboxylation of various aromatic carboxylic acids catalyzed by Pd(II) has been developed in this work. A series of electron-rich arenecarboxylic acids gave the corresponding decarboxylative monohalogenation products under the typical reaction conditions.
Room-temperature synthesis of tetra-ortho-substituted biaryls by NHC-catalyzed Suzuki-Miyaura couplings
Wu, Linglin,Drinkel, Emma,Gaggia, Fiona,Capolicchio, Samanta,Linden, Anthony,Falivene, Laura,Cavallo, Luigi,Dorta, Reto
supporting information; experimental part, p. 12886 - 12890 (2011/12/15)
Into the groove: The introduction of a C2-symmetric N-heterocyclic carbene ligand with appropriately substituted naphthyl side chains enables the efficient Suzuki-Miyaura coupling to form bulky tetra-ortho-substituted biaryls from aryl bromides and chlorides at room temperature. DFT calculations uncover the subtle steric phenomena at play that lead to the superior catalytic performance. Cyoct=cyclooctyl. Copyright
Catalytic Halogenation of Selected Organic Compounds Mimicking Vanadate-dependent Marine Metalloenzymes
Dinesh, Chimmanamada U.,Kumar, Rajiv,Pandey, Bipin,Kumar, Pradeep
, p. 611 - 612 (2007/10/02)
The ammonium metavanadate, mimicking vanadate-dependent metalloenzymes, efficiently catalyses the halogenation of a variety of organic substrates in dilute conditions in moderate to good yields using dilute hydrogen peroxide (30percent) as an oxidizing agent exhibiting remarkable ortho selectivity with electron-rich aromatics.
Selective Preparation of 1-Halo-2,6-dimethoxybenzenes from Bis(2,6-dimethoxyphenyl)dimethyltin
Wada, Masanori,Wakamori, Hiroyuki,Hiraiwa, Akira,Erabi, Tatsuo
, p. 1389 - 1391 (2007/10/02)
With a hope to explore a facile method for preparation of 1-halo-2,6-dimethoxybenzenes, bis(2,6-dimethoxyphenyl)dimethyltin was prepared from 1,3-dimethoxybenzene, butyllithium, and dimethyltin dichloride or dimethyltin sulfide.The compound reacted with N
Formation and Structure of Bis(2,6-dimethoxyphenyl)nitramine, 2NNO2
Heuer, Lutz,Schmutzler, Reinhard,Schomburg, Dietmar
, p. 911 - 916 (2007/10/02)
Bis(2,6-dimethoxyphenyl)nitramine (1) was found to be one of the products of the reaction of nitryl chloride, NO2Cl with 2,6-dimethoxyphenyl lithium. 1 was characterized through its NO2 vibrations in the IR spectrum, νas = 1540 cm-1 and νs = 1290 cm-1, and its identity was confirmed by its elemental analysis, 1H and 13C NMR data, and its mass spectrum.According to a single crystal X-ray structure determination, 1 is nearly planar about the central N-N bond; the N-N bond length is 136.3 pm.In addition, two further products of the reaction were also characterized, 1-chloro-2,6-dimethoxybenzene (2) and 2,4-dichloro-1,5-dimethoxybenzene (3). - Keywords: Aryllithium Compounds, Nitryl Chloride, Nitramines, X-Ray Structure
