10229-11-5Relevant articles and documents
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Danehy,Vogt,Nieuwland
, p. 2327 (1935)
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Synthesis of palladated magnetic nanoparticle (Pd@Fe3O4/AMOCAA) as an efficient and heterogeneous catalyst for promoting Suzuki and Sonogashira cross-coupling reactions
Tamoradi, Taiebeh,Daraie, Mansoureh,Heravi, Majid M.
, (2020)
Palladium supported magnetic nanoparticle (Pd@Fe3O4/AMOCAA) was easily prepared in the presence of Scrophularia striata extract and fully characterized by FT-IR, SEM, VSM, TEM, TGA, XRD and EDAX. It was successfully employed as an easily separable and reusable effective heterogeneous catalyst classical Suzuki and Sonogashira cross-coupling reaction. Sustainability of the methodology was reserved by easy recovery of the catalyst using an external magnet and reusing it for 7 times without appreciable loss of its catalytic activity.
Tributylmanganate(II)-mediated cyclization of enynes
Usugi,Shinokubo,Oshima
, p. 1903 - 1904 (2000)
Treatment of enynes with tributylmanganate(II) provided cyclized products containing alkylidene substituents. 1-Tridecen-6-yne or 1-tetradecen-7-yne gave 1-heptylidene-2-methylcyclopentane or 1-heptylidene-2-methylcyclohexane in 67 or 50% yield, respectiv
A functionalized ionic liquid containing phosphine-ligated palladium complex for the Sonogashira reactions under aerobic and CuI-free conditions
Zhang, Jing,Crossed, Dakovi? Marijana,Popovi?, Zora,Wu, Haihong,Liu, Ye
, p. 160 - 163 (2012)
A Pd-complex functionalized ionic liquid (IL), di-(1-butyl-2- diphenylphosphino-3-methylimidazolium)-dichloropalladium(II) hexafluorophosphate (2), was synthesized and used as the highly efficient and recyclable catalyst for the Sonogashira reactions of aryl iodides and aryl bromides with several terminal acetylenes, under aerobic and CuI-free conditions. The activity loss, Pd black precipitation, and Pd leaching were not observed even after 7 runs in 2-catalyzed Sonogashira reactions using the room temperature IL of [Bmim]PF 6 as the reaction medium.
Thiol addition to aryl propargyl alcohols under mild conditions: An accelerating neighboring group effect
See Waters, Marjorie,Cowen, Jennifer A.,McWilliams, J. Christopher,Maligres, Peter E.,Askin, David
, p. 141 - 144 (2000)
Aryl alkynols provide a convenient entry into α-hydroxyketones via thiol addition followed by hydrolysis. Thiols have been added to several non- activated alkynes under mild, basic conditions. A coordinating functional group in close proximity to the triple bond facilitates this reaction.
Amphiphilic ionic palladium complexes for aqueous-organic biphasic Sonogashira reactions under aerobic and CuI-free conditions
Wang, Xuezhu,Zhang, Jing,Wang, Yongyong,Liu, Ye
, p. 23 - 26 (2013)
The ionic Pd(II)-complexes of 2 (ammonium-[1-(2-hydroxyethyl)-3- methylimidazolium] bis[3-(diphenylphosphino)benzenesulfonate]- dichloropalladium(II) ([(NH4)(Hemim)][PdCl2(TPPMS) 2])) and 3 (bis[1-n-butyl-3-methylimidazolium] bis[3- (diphenylphosphino)benzenesulfonate]-dichloropalladium(II) ([Bmim] 2[PdCl2(TPPMS)2])) were synthesized and fully characterized. The single crystal X-ray diffraction analyses show that 2 and 3 are composed of the imidazolium-based cations and [PdCl2(TPPMS) 2]2 - anions. The properties of such imidazolium-based Pd-complexes of 2 and 3, in terms of the aqueous solubilities and the catalytic behaviors in water, could be dramatically varied. When 2 and 3 were applied as the precatalysts for the Sonogashira coupling of iodobenzene with phenylacetylene under aerobic and CuI-free conditions, the much higher yields of 1,2-diphenylethyne were obtained due to their amphiphilicity. The wide generality of 2 was available for aqueous-organic biphasic Sonogashira reactions.
On the catalytic duo PdCl2(PPh3)2/AuCl(PPh3) that cannot effect a Sonogashira-type reaction: a correction
Panda, Biswajit,Sarkar, Tarun K.
, p. 301 - 305 (2010)
In contrast to the observation made by the Laguna group, we report that the combination of PdCl2(PPh3)2 and AuCl(PPh3) makes a unique catalytic system that allows Sonogashira-type cross-coupling of both aryl and alkyl alkynes with aryl halides in excellent yields.
Sonogashira reaction of aryl and heteroaryl halides with terminal alkynes catalyzed by a highly efficient and recyclable nanosized MCM-41 anchored palladium bipyridyl complex
Lin, Bo-Nan,Huang, Shao-Hsien,Wu, Wei-Yi,Mou, Chung-Yuan,Tsai, Fu-Yu
, p. 9157 - 9173 (2010)
A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using low Pd loadings to 0.01 mol%, and the nanosized MCM-41-Pd catalyst was recovered by centrifugation of the reaction solution and re-used in further runs without significant loss of reactivity.
Easy copper-, ligand- and amine-free sonogashira coupling reaction catalyzed by palladium on carbon at low catalyst loading and by exposure to air
Zhang, Guolin
, p. 619 - 622 (2005)
An easy copper-, ligand and amine-free Sonogashira coupling reaction catalyzed by commercially available palladium on carbon with air at low catalyst loading (0.2 mol% Pd) has been developed. Aryl iodides coupled with aromatic alkynes gave good to excelle
Polyoxometalate-Gold(I)/H+ Complexes: Air-Stable, Efficient, Polyvalent, and Bifunctional Catalysts
Hueber, Damien,Hoffmann, Marie,De Frémont, Pierre,Pale, Patrick,Blanc, Aurélien
, p. 5065 - 5072 (2015)
Gold(I)/H+-polyoxometalate hybrids, with general formula [POM]x-[H]x-1+[R3PAu(MeCN)]+, were synthesized and fully characterized by 31P and 29Si MAS or liquid NMR, FT-I
An efficient palladium-catalysed reaction of vinyl and aryl halides or triflates with terminal alkynes
Alami,Ferri,Linstrumelle
, p. 6403 - 6406 (1993)
In the presence of tetrakis(triphenylphosphine)palladium, vinyl and aryl halides or triflates react very rapidly in piperidine or pyrrolidine with terminal alkynes to give conjugated enynes and aryl acetylenes in high yields.
A phenyldithiocarbazate-functionalized polyvinyl chloride resinsupported Pd(II) complex as an effective catalyst for solvent- and copper-free Sonogashira reactions under aerobic conditions
Bakherad, Mohammad,Keivanloo, Ali,Samangooei, Shahrzad,Omidian, Mina
, p. 78 - 82 (2013)
The PVC-supported phenyldithiocarbazate palladium complex was prepared and characterized. The catalyst exhibits excellent catalytic activity and stability for the Sonogashira coupling reaction under ambient conditions. Various terminal alkynes were coupled with a number of aryl halides in the presence of 1.0 mol% of the catalyst to afford the corresponding products in high yields. Furthermore, the heterogeneous catalyst can be readily recovered by simple filtration and reused for several times without a significant loss in its activity.2013 Elsevier B.V. All rights reserved.
Synthesis of Polysubstituted Fused Pyrroles by Gold-Catalyzed Cycloisomerization/1,2-Sulfonyl Migration of Yndiamides
Smith, Philip J.,Jiang, Yubo,Tong, Zixuan,Pickford, Helena D.,Christensen, Kirsten E.,Nugent, Jeremy,Anderson, Edward A.
supporting information, p. 6547 - 6552 (2021/08/30)
Yndiamides (bis-N-substituted alkynes) are valuable precursors to azacycles. Here we report a cycloisomerization/1,2-sulfonyl migration of alkynyl-yndiamides to form tetrahydropyrrolopyrroles, unprecedented heterocyclic scaffolds that are relevant to medicinal chemistry. This functional group tolerant transformation can be achieved using Au(I) catalysis that proceeds at ambient temperature, and a thermally promoted process. The utility of the products is demonstrated by a range of reactions to functionalize the fused pyrrole core.
Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy
Zhang, Bo-Sheng,Wang, Fan,Gou, Xue-Ya,Yang, Ying-Hui,Jia, Wan-Yuan,Liang, Yong-Min,Wang, Xi-Cun,Li, Yuke,Quan, Zheng-Jun
supporting information, p. 7518 - 7523 (2021/10/01)
In palladium/norbornene (Pd/NBE) chemistry, the "ortho effect"has been proven to be a key factor in the process of β-carbon elimination to extrude NBE. Herein, we found that the o-iodoaniline protected by a p-methoxybenzenesulfonyl group can recover the "
