16616-43-6Relevant articles and documents
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.).
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
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.
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.
Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines
Luo, Xiaosheng,Wang, Ping
, p. 4960 - 4965 (2021/07/20)
Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.
Straightforward Stereoselective Synthesis of Seven-Membered Oxa-Bridged Rings through in Situ Generated Cycloheptenol Derivatives
Wang, Mengdan,Yin, Liqiang,Cheng, Lu,Yang, Yajie,Li, Yanzhong
, p. 12956 - 12963 (2021/09/13)
An iodine-mediated stereoselective synthesis of seven-membered oxa-bridged rings via in situ generated cycloheptenols was reported. This process was realized through the combination of C-C σ-bond cleavage and C-O bond-forming reactions in a one-pot fashion from simple and easily accessible raw materials. The formation of carbon radicals initiated by I2 was the key to the reaction.