4416-67-5Relevant academic research and scientific papers
Direct C-H Cyanation of Arenes via Organic Photoredox Catalysis
McManus, Joshua B.,Nicewicz, David A.
, p. 2880 - 2883 (2017/03/11)
Methods for the direct C-H functionalization of aromatic compounds are in demand for a variety of applications, including the synthesis of agrochemicals, pharmaceuticals, and materials. Herein, we disclose the construction of aromatic nitriles via direct C-H functionalization using an acridinium photoredox catalyst and trimethylsilyl cyanide under an aerobic atmosphere. The reaction proceeds at room temperature under mild conditions and has proven to be compatible with a variety of electron-donating and -withdrawing groups, halogens, and nitrogen- and oxygen-containing heterocycles, as well as aromatic-containing pharmaceutical agents.
A Mild and Selective Method for the Catalytic Hydrodeoxygenation of Cyanurate Activated Phenols in Multiphasic Continuous Flow
Zhao, Yuhan,King, Georgina,Kwan, Maria H.T.,Blacker, A. John
supporting information, p. 2012 - 2018 (2017/02/10)
A low-energy, high-selectivity approach to the catalytic hydrodeoxygenation of phenols is reported using batch or continuous flow methods to react 3 equiv of phenol with cyanuric chloride then hydrogenolyzing the triarylcyanurate intermediate to give 3 equiv of deoxo aromatic. The use of cyanuric chloride compares favorably with existing activation methods, showing improved scalability, atom efficiency, and economics. The scope of both the activation and hydrogenolysis stages are explored using lignin-related phenols. Initial development has identified that continuous stir tank reactors (CSTRs) enable a multiphasic process for converting guaiacol to anisole and at steady state overcome the catalyst deactivation issues observed in batch, seemingly caused by the cyanurate byproduct. Green chemistry aspects and the potential for industrial adoption are discussed.
Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates
Lei, Xiangyang,Jalla, Anusha,Abou Shama, Mhd A.,Stafford, Jamie M.,Cao, Billy
supporting information, p. 2578 - 2585 (2015/09/01)
Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding
Dimerization of Aryl Sulfonates by in situ Generated Nickel(0)
Maddaluno, Jacques,Durandetti, Muriel
supporting information, p. 2385 - 2388 (2015/10/19)
A mild and user-friendly nickel-catalyzed method for the reductive homocoupling of aromatic tosylates is presented. The reaction proceeds between room temperature and 60 °C, with stable substrates (ArOTs) easily prepared from inexpensive and commercially available phenols or naphthols. It relies on a catalytic amount (10 mol%) of a robust catalyst (NiBr2bipy) that does not require the preparation of sensitive organometallic intermediates. Yields are good to excellent.
Aminocarbonylation of Aryl Tosylates to Carboxamides
Chung, Seungwon,Sach, Neal,Choi, Chulho,Yang, Xiaojing,Drozda, Susan E.,Singer, Robert A.,Wright, Stephen W.
supporting information, p. 2848 - 2851 (2015/06/16)
The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.
Iridium-catalyzed dehydrogenative decarbonylation of primary alcohols with the liberation of syngas
Olsen, Esben P. K.,Madsen, Robert
, p. 16023 - 16029 (2013/02/22)
A new iridium-catalyzed reaction in which molecular hydrogen and carbon monoxide are cleaved from primary alcohols in the absence of any stoichiometric additives has been developed. The dehydrogenative decarbonylation was achieved with a catalyst generated in situ from [Ir(coe)2Cl]2 (coe=cyclooctene) and racemic 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (rac-BINAP) in a mesitylene solution saturated with water. A catalytic amount of lithium chloride was also added to improve the catalyst turnover. The reaction has been applied to a variety of primary alcohols and gives rise to products in good to excellent yields. Ethers, esters, imides, and aryl halides are stable under the reaction conditions, whereas olefins are partially saturated. The reaction is believed to proceed by two consecutive organometallic transformations that are catalyzed by the same iridium(I)-BINAP species. First, dehydrogenation of the primary alcohol to the corresponding aldehyde takes place, which is then followed by decarbonylation to the product with one less carbon atom.
Highly efficient Pd-catalyzed cyanation of aryl chlorides and arenesulfonates with potassium ferrocyanide in aqueous media
Zhang, Junli,Chen, Xiaorong,Hu, Tongjie,Zhang, Yuan,Xu, Kunling,Yu, Yanpeng,Huang, Jun
experimental part, p. 56 - 60 (2011/01/12)
A highly improved Pd-catalyzed cyanation of aryl chlorides to corresponding benzonitriles was demonstrated in aqueous media. Moreover, Pd-catalyzed cyanation of aryl tosylates and benzenesulfonates with K4[Fe(CN) 6] was developed under the similar conditions, which extended application scope of the cyanation. Graphical Abstract: [Figure not available: see fulltext.]
Synthesis and characterization of triphenylene derivatives containing two terminal functional groups at the periphery
Wan,Wang,Jiang,Hao
, p. 42 - 56 (2008/09/20)
Three novel series of triphenylene-based derivatives possessing functional group (ester, carboxylic acid, or hydroxy) at the ends of two aliphatic chains on the opposite position of triphenylene core have been synthesized and studied on mesomorphic proper
Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates
Schade, Matthias A.,Metzger, Albrecht,Hug, Stephan,Knochel, Paul
supporting information; experimental part, p. 3046 - 3048 (2009/02/04)
Benzylic zinc reagents prepared by direct insertion of zinc to benzylic chlorides in the presence of LiCl undergo smooth cross-coupling reactions with aromatic chlorides, bromides and tosylates using Ni(acac)2 and PPh3 as a catalyst
A new preparative method of aryl sulfonate esters by using cyclic organobismuth reagents
Sakurai, Naoto,Mukaiyama, Teruaki
, p. 771 - 790 (2008/09/18)
A new method for the preparation of aryl sulfonate esters by using a cyclic pentavalent bismuth is described. Aryl sulfonate esters are formed in good to high yields by treating 10-arylphenothiabismine 5,5-dioxides, m-chloroperoxybenzoicacid (m-CPBA)and various sulfonic acids in dichloromethane.
