16616-43-6Relevant academic research and scientific papers
Direct Decarboxylative Alkynylation of α,α-Difluoroarylacetic Acids under Transition Metal-Free Conditions
Li, Xiang,Li, Siyu,Sun, Suyan,Yang, Fan,Zhu, Weiguo,Zhu, Yu,Wu, Yusheng,Wu, Yangjie
, p. 1699 - 1704 (2016)
An efficient and generally applicable protocol for decarboxylative coupling of α,α-difluoroarylacetic acids with ethynylbenziodoxolone (EBX) reagents has been developed, affording α,α-difluoromethylated alkynes bearing various functional groups in moderate to excellent yields. Remarkably, this potassium persulfate (K2S2O8)-promoted reaction employs water as solvent under transition metal-free conditions, thus providing a green synthetic approach to α,α-difluoromethylated alkynes. (Figure presented.).
Bifunctional ligands in combination with phosphines and Lewis acidic phospheniums for the carbonylative Sonogashira reaction
Tan, Chen,Wang, Peng,Liu, Huan,Zhao, Xiao-Li,Lu, Yong,Liu, Ye
, p. 10871 - 10874 (2015)
The combination of phosphine-ligated Pd catalysis and phosphenium(v) Lewis acid catalysis has been developed for the carbonylative Sonogashira reaction using phosphino-phosphenium salts (L1-L4) as bifunctional ligands, in which the Lewis acidic phospheniu
Copper-catalyzed, palladium-free carbonylative Sonogashira coupling reaction of aliphatic and aromatic alkynes with iodoaryls
Tambade, Pawan J.,Patil, Yogesh P.,Nandurkar, Nitin S.,Bhanage, Bhalchandra M.
, p. 886 - 888 (2008)
Copper bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed carbonylative Sonogashira coupling reactions of aliphatic/aromatic alkynes with iodoaryls are reported for the first time. The protocol eliminates the use of a toxic, air-sensitive, and expensiv
Palladium-catalyzed alkynylcarbonylation of aryl iodides with the use of Mo(CO)6 in the presence of tBu3P ligand
Iizuka, Muneaki,Kondo, Yoshinori
, p. 5180 - 5182 (2007)
Palladium-catalyzed alkynylcarbonylation of aryl iodides was accomplished by using Mo(CO)6 as a CO source. The reaction was conducted at room temperature with the use of tBu3P as a ligand, which was found to be essential for smooth c
Ionic palladium complex as an efficient and recyclable catalyst for the carbonylative Sonogashira reaction
Yang, Da,Wang, Dongliang,Liu, Huan,Zhao, Xiaoli,Lu, Yong,Lai, Shijun,Liu, Ye
, p. 405 - 411 (2016)
The neutral palladium(II) complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-imidazolyl] dichloropalladium(II) (1A) ligated by thiazolylimidazolyl-based phosphine (L1) in which thiazolylimidazolyl acted as an S- and N-donor provider with weak coordinating nature, and the ionic complex bis-[1-(5'-diphenylphosphinothiazol-2'-yl)-3-methylimidazolium] dichloropalladium(II) trifluoromethanesulfonate (2A) ligated by thiazolylimidazolium-based phosphine (L2) after quaternization of L1 using methyl trifluoromethanesulphonate were synthesized. It was found that the introduced positive charges and strong electron-withdrawing effect in 2A not only led to changes in the configuration and structural stability of the complex, but also lowered its catalytic performance in carbonylative Sonogashira reactions. These effects reveal the important role of the N-donor in 1A. In addition, as an ionic palladium complex, 2A combined with the room-temperature ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate could be recycled eight times as the catalyst in carbonylative Sonogashira reactions without detectable metal leaching.
Robust alkyl-bridged bis(N-heterocyclic carbene)palladium(II) complexes anchored on Merrifield's resin as active catalysts for the selective synthesis of flavones and alkynones
Mansour, Waseem,Fettouhi, Mohammed,Saleem, Qasim,El Ali, Bassam
, (2021)
Highly active and efficient propylene-bridged bis(N-heterocyclic carbene)palladium(II) complexes covalently anchored on Merrifield's resin were synthesized and characterized using various physical and spectroscopic techniques. The two anchored Pd(II) complexes consist of the system: Merrifield's resin-linker-bis(NHC)Pd(II), the linkers being benzyl and benzyl-O-(CH2)3 for (Pd-NHC1@M) and (Pd-NHC2@M), respectively. The short linker anchored bis-benzimidazolium ligand precursor (PBBI-1@M) was synthesized via direct carbon–nitrogen alkylation of a propylene-bridged bis(benzimidazole) (PBBI-1) by Merrifield's resin chlorobenzyl group. The longer linker anchored bis-benzimidazolium ligand precursor (PBBI-2@M) was obtained in a two-step reaction involving first alkylation of (PBBI-1) with 3-chloro-1-propanol followed by a nucleophilic substitution at Merrifield's resin chlorobenzyl group. Both supported ligand precursors (PBBI-1@M and PBBI-2@M) reacted with palladium acetate to produce the two heterogeneous catalysts (Pd-NHC1@M) and (Pd-NHC2@M). 13C NMR palladation shift of the benzimidazole N–C–N (C2) carbon was found very similar in both the liquid NMR spectra of the homogeneous complexes and the CP/MASS spectra of the corresponding covalently anchored complexes. The catalytic activity, stability, and the recycling ability of the supported catalysts have been investigated in the carbonylative Sonogashira coupling reactions of aryl iodides with aryl alkynes and alkyl alkynes and also in the cyclocarbonylative Sonogashira coupling reactions of aryl iodides with aryl alkynes via one pot reactions. The longer linker catalyst Pd-NHC2@M demonstrated excellent catalytic activity, stability, and very high recycling ability in the two carbonylative coupling reactions. These systems exhibit the hypothesized thermodynamic stability offered by the chelate effect in addition to the strong sigma donor ability of a bis(NHC) ligand system generating electron-rich palladium centers that favor the oxidative addition step of the aryl halide.
REACTIONS OF ARYL AND HETERYL IODIDES WITH TERMINAL ACETYLENES IN THE PRESENCE OF CO, CATALYZED BY PALLADIUM COMPLEXES
Ponomarev, A.B.,Shostakovskii, M.V.,Kalinin, V.N.
, p. 2224 - 2227 (1991)
The influence of the nature of the solvent, of the base, the catalyst, the temperature, and the pressure of CO on reactions of aryl and heteryl iodides RI with terminal acetylenes R'CCH in the presence of CO, catalyzed by palladium complexes is studied.
Organoborane-catalyzed selective 1,2-reduction of alkynones with hydride transfer: Synthesis of benzyl alkynes
Zhai, Lele,Yang, Zhigang,Man, Qinghong,Yang, Mingyu,Ren, Yangqing,Wang, Lei,Li, Huilin,She, Xuegong
, (2022/01/28)
Benzyl alkynes are important organic building blocks in organic synthesis. We report herein a B(C6F5)3-catalyzed site-selective 1,2-reduction of readily available alkynones to access benzyl alkyne derivatives. Under the de
Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones
He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo
supporting information, p. 457 - 466 (2021/01/29)
An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is
Synthesis of Isoselenazoles and Isothiazoles from Demethoxylative Cycloaddition of Alkynyl Oxime Ethers
Zhang, Zhu-Zhu,Chen, Rong,Zhang, Xiao-Hong,Zhang, Xing-Guo
, p. 632 - 642 (2020/12/22)
A general method for the synthesis of isoselenazoles and isothiazoles has been developed by the base-promoted demethoxylative cycloaddition of alkynyl oxime ethers using the cheap and inactive Se powder and Na2S as selenium and sulfur sources. This transformation features the direct construction of N-, Se-, and S-containing heterocycles through the formation of N-Se/S and C-Se/S bonds in one-pot reactions with excellent functional group tolerance.
