123770-67-2Relevant academic research and scientific papers
Palladium nanoparticles supported on MOF-5: A highly active catalyst for a ligand- and copper-free Sonogashira coupling reaction
Gao, Shuixia,Zhao, Nan,Shu, Mouhai,Che, Shunai
, p. 196 - 201 (2010)
Palladium nanoparticles supported on MOF-5 (Pd/MOF-5), have been prepared by a chemical method at room temperature. MOF-5 and Pd/MOF-5 were characterized by X-ray diffraction, N2 sorption, thermogravimetric analysis, scanning electron microscopy, and transmission electron microscopy. The catalyst consists of highly dispersed palladium nanoparticles (about 3-6 nm) on MOF-5 with a high surface area (533 m2/g). It exhibits efficient catalytic activity for the Sonogashira coupling reaction between aryl iodides and terminal acetylenes without the assistance of ligand and copper.
Bis(μ-iodo)bis((-)-sparteine)dicopper(I) catalyzed Sonogashira-type reaction under palladium and phosphine-free conditions
Priyadarshini,Joseph, P.J. Amal,Srinivas,Maheswaran,Kantam, M. Lakshmi,Bhargava, Suresh
, p. 1615 - 1618 (2011)
An efficient and inexpensive protocol for the Sonogashira-type cross coupling reactions of phenylacetylenes with a variety of haloarenes including activated aryl chlorides employing the structurally well-characterized bis(μ-iodo)bis((-)-sparteine)dicopper
Copper-free sonogashira coupling reaction with PdCl2 in water under aerobic conditions
Liang, Bo,Dai, Mingji,Chen, Jiahua,Yang, Zhen
, p. 391 - 393 (2005)
(Chemical Equation Presented). A mild protocol for the copper-free Sonogashira coupling of aryl iodides with terminal acetylenes in water under aerobic conditions has been developed. The use of 1 mol % PdCl2 in the presence of pyrrolidine allows the coupling reaction to proceed at room temperature or 50°C with good to excellent yields.
Palladium/copper-catalyzed sila-Sonogashira reactions of aryl iodides with alkynylsilanes via a direct C-Si bond activation
Nishihara, Yasushi,Inoue, Eiji,Ogawa, Daisuke,Okada, Yoshiaki,Noyori, Shintaro,Takagi, Kentaro
, p. 4643 - 4646 (2009)
The palladium-catalyzed cross-coupling reactions of aryl iodides with alkynylsilanes in the presence of a substoichiometric amount (50 mol %) of copper(I) chloride as an activator in DMF under strictly non-basic reaction conditions afford the corresponding unsymmetrical diarylethynes in moderate to excellent yields. A wide range of substrates bearing an electron-donating or an electron-withdrawing substituent on the aromatic ring are compatible.
Copper-catalyzed cross-coupling of aryl iodides and aryl acetylenes using microwave heating
He, Huan,Wu, Yong-Jin
, p. 3237 - 3239 (2004)
An efficient copper-catalyzed cross-coupling of aryl iodides with aryl acetylenes under microwave irradiation is described. The reaction proceeds under microwave heating with 10mol% CuI and 2equiv Cs2CO3 in 43-87% yields.
Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes
Nishihara, Yasushi,Ikegashira, Kazutaka,Hirabayashi, Kazunori,Ando, Jun-Ichi,Mori, Atsunori,Hiyama, Tamejiro
, p. 1780 - 1787 (2000)
Reaction of 1-trimethylsilylalkyne with copper(I) chloride in a polar solvent, DMF, at 60 °C under an aerobic conditions smoothly undergoes homo- coupling to give the corresponding symmetrical 1,3-butadiynes in 70-99% yields. In addition, (arylethynyl)trimethylsilanes are found to couple with aryl triflates and chlorides in the presence of Cu(I)/Pd(0) (10 mol %/5 or 10 mol %) cocatalyst system to give the corresponding diarylethynes in 49-99% yields. The cross-coupling reaction is applied to a one-pot synthesis of the corresponding unsymmetrical diarylethynes from (trimethylsilyl)ethyne via sequential Sonogashira-Hagihara and the present cross-coupling reactions using two different aryl triflates. The reactions of (arylethynyl)trimethylsilanes with aryl(chloro)ethynes in the presence of 10 mol % of CuCl also yield the corresponding unsymmetrical 1,3-butadiynes in 43-97% yields.
Polymethylhydrosiloxane (PMHS) as an additive in Sonogashira reactions
Gallagher, William P.,Maleczka Jr., Robert E.
, p. 537 - 541 (2003)
Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the Sonogashira reaction of a variety of alkynes and electrophiles. These couplings appear to involve the in situ formation and reaction of an alkynylsiloxane. Such couplings can be run am
Ruthenium-catalyzed C-H silylation of methylboronic acid using a removable α-directing modifier on the boron atom
Ihara, Hideki,Ueda, Akinori,Suginome, Michinori
, p. 972 - 974 (2011)
Ruthenium-catalyzed C-H silylation of methylboronic acid was achieved by use of 2-(1H-pyrazol-3-yl)aniline as a removable α-directing modifier on the boron atom. Crosscoupling of the product, i.e., (phenyldimethylsilyl) methylpinacolborane, with aryl halides proceeded in the presence of a [PdCl 2(dppf)] catalyst and CsOH as a base.
Cu(I)/Pd(0)-catalyzed cross-coupling reaction of alkynylsilanes with aryl or alkenyl triflates: "Sila"-Sonogashira-Hagihara coupling
Nishihara, Yasushi,Ikegashira, Kazutaka,Mori, Atsunori,Hiyama, Tamejiro
, p. 1233 - 1234 (1997)
Alkynylsilanes reacted with aryl or alkenyl triflates in the presence of 5 mol% of Pd(PPh3)4 and 10 mol% of CuCl in DMF to give the corresponding cross-coupling, namely "sila"-Sonogashira-Hagihara coupling, products in good to excell
Palladium-catalyzed decarbonylative sonogashira coupling of terminal alkynes with carboxylic acids
Chen, Tieqiao,Huang, Tianzeng,Li, Chunya,Li, Wenhui,Li, Xinyi,Li, Zhaohui,Liu, Long,Tang, Zhi,Zhang, Tao
supporting information, p. 3304 - 3309 (2021/05/31)
A direct decarbonylative Sonogashira coupling of terminal alkynes with carboxylic acids was achieved through palladium catalysis. This reaction did not use overstoichiometric oxidants, thus overcoming the homocoupling issue of terminal alkynes. Under the reaction conditions, a wide range of carboxylic acids including those bioactive ones could couple readily with various terminal alkynes, thus providing a relative general method for preparing internal alkynes.
