124643-34-1Relevant academic research and scientific papers
Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide
Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven
supporting information, p. 17887 - 17896 (2020/08/19)
An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.
Practical Ni-Catalyzed Cross-Coupling of Unsaturated Zinc Pivalates with Unsaturated Nonaflates and Triflates
Hofmayer, Maximilian S.,Lutter, Ferdinand H.,Grokenberger, Lucie,Hammann, Jeffrey M.,Knochel, Paul
supporting information, p. 36 - 39 (2019/01/04)
A practical nickel-catalyzed cross-coupling of (hetero)aryl or alkynylzinc pivalates with various unsaturated nonaflates or triflates is described. Organozinc pivalates allow these cross-couplings to take place with high yields and a low catalyst loading (0.5 mol %). Couplings with (E)- and (Z)-alkenyl triflates proceed with retention of configuration.
Ni/Ti Dual Catalytic Cross-Coupling of Nitriles and Organobromides to Access Ketones
Chenniappan, Vinoth Kumar,Silwal, Sajan,Rahaim, Ronald J.
, p. 4539 - 4544 (2018/05/23)
Herein, we report the development of a dual catalytic approach for the cross-coupling of nitriles with aryl- and aliphatic-bromides. A titanium(III) catalyst is used to activate nitriles enabling their coupling with organobromides through a nickel catalyst. The Ni/Ti system efficiently prepared unsymmetrical ketones with good chemoselectivity and could selectively couple a bromide in the presence of other functionalizable handles.
Ligand- and Solvent-Tuned Chemoselective Carbonylation of Bromoaryl Triflates
Shen, Chaoren,Wei, Zhihong,Jiao, Haijun,Wu, Xiao-Feng
, p. 13369 - 1337 (2017/09/06)
The palladium-catalyzed chemoselective carbonylation of bromoaryl triflates is reported. The selective C?Br bond versus C?OTf (OTf=triflate) bond functionalization can be remarkably tuned by the combination of the ligand [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) vs. 1,1′-bis(diphenylphosphino)ferrocene (DPPF)] and the solvent (toluene vs. DMSO). The respective ligand and solvent effects are rationalized by DFT calculations. In contrast, the monodentate ligands BuPAd2 and tBu3P prefer the selective C?Br bond activation and are solvent insensitive.
Highly active catalysts of bisphosphine oxides for asymmetric Heck reaction
Hu, Jian,Lu, Yunpeng,Li, Yongxin,Zhou, Jianrong
supporting information, p. 9425 - 9427 (2013/10/01)
Bisphosphine oxides formed highly active asymmetric Heck catalysts, which were applied in asymmetric synthesis of pharmacologically active azacycles. Olefin insertion proceeded via cis pathways, different from P,N-ligands.
Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins
Wu, Xiaojin,Lu, Yunpeng,Hirao, Hajime,Zhou, Jianrong
supporting information, p. 6014 - 6020 (2013/06/26)
In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright
Synthesis and biochemical evaluation of a series of trifluoromethanesulfonate derivatives of 4 hydroxyphenyl ketones - Probes of the active site of type 1 and 3 of the 17β-hydroxysteroid dehydrogenase family of enzymes
Olusanjo, Moniola S.,Cartledge, Timothy,Shah, Kruti,Ahmed, Sabbir
, p. 253 - 259 (2013/01/10)
In an effort to aid the design of 'dual-inhibitors' of types 1 and 3 of the 17β-hydroxysteroid dehydrogenase (17β-HSD), we report the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of trifluoromethanesulfonate derivatives of 4-hydroxyphenyl ketone-based compounds which were found to be weak inhibitors of types 1 and 3.
Aminations of aryl bromides in water at room temperature
Lipshutz, Bruce H.,Chung, David W.,Rich, Brian
supporting information; experimental part, p. 1717 - 1721 (2011/03/20)
Unsymmetrical di- and triarylamines can be formed under green chemistry conditions, taking advantage of micellar catalysis leading to palladium-catalyzed aminations at ambient temperatures in water as the only medium.
Aryl triflates: Useful coupling partners for the direct arylation of heteroaryl derivatives via Pd-catalyzed C-H activation-functionalization
Roger, Julien,Doucet, Henri
, p. 169 - 174 (2008/09/20)
Aryl triflates were found to be suitable partners for the palladium catalyzed direct arylation of heteroaromatics via C-H activation- functionalization. The reaction conditions and the catalyst have a determining influence on the yields. The system combining PPh3 and Pd(OAc) 2 using KOAc as base and DMF as solvent promotes the selective 2- or 5-arylations in moderate to high yields. Several heteroaromatics such as furan, thiophene, thiazole or oxazole derivatives have been employed successfully. The electronic properties of the aryl triflates also have a decisive influence on the yields of the coupling products. Electron-rich aryl triflates gave satisfactory results, whereas the electron-poor ones led to the formation of phenols. The Royal Society of Chemistry 2008.
Cationic palladium(II)-catalyzed addition of arylboronic acids to nitriles. One-step synthesis of benzofurans from phenoxyacetonitriles
Zhao, Baowei,Lu, Xiyan
, p. 5987 - 5990 (2007/10/03)
(Chemical Equation Presented) A cationic palladium complex catalyzed addition of arylboronic acids to nitrites to yield aryl ketones with moderate to good yields was developed. A one-step synthesis of benzofurans from phenoxyacetonitriles under the catalysis of [(bpy)Pd+(μ-OH)] 2(-OTf)2 or [(bpy)Pd2+(H 2O2)2](-OTf)2 was developed which showed that the cationic palladium catalyst is highly active for these addition reactions.
