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
Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide
Wu, Haopeng,Shao, Chukai,Wu, Di,Jiang, Liang,Yin, Hongquan,Chen, Fu-Xue
, p. 5327 - 5335 (2021/04/06)
A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.
