103-30-0Relevant articles and documents
Palladium-catalyzed cross-coupling of Cr(CO)3-complex chloroarenes with organofluorosilanes
Kang, Suk-Ku,Kim, Won-Yeob
, p. 3743 - 3749 (1998)
The palladium-catalyzed cross-coupling of (η6-chlorobenzene) tricarbonylchromium complexes with organofluorosilanes followed by decomplexation afforded aryl-, alkenyl-, and alkynyl-substituted arenes.
New studies of Rh-catalyzed addition of boronic acids under basic conditions in aqueous medium
Amengual, Rémi,Michelet, Véronique,Genêt, Jean-Pierre
, p. 5905 - 5908 (2002)
Rh-catalyzed C-C bond formation in neat water under basic conditions has been efficiently performed. The addition of various boronic acids to styrene, 2-vinylpyridine, and cyclic α,β-unsaturated ketones has been realized with high selectivity and yield. We have shown that m-TPPTC (tris(m-carboxyphenyl)phosphane trilithium salt) exhibited a higher reactivity compared to TPPTS. These couplings could also be conducted very efficiently under basic and phosphaneless conditions to give functionalized aryl derivatives. The benefits of the additional anionic ligand m-TPPTC lied in the successful recycling experiments of 1,4-addition of phenylboronic acid to cyclohexenone, with no loss of the water-soluble catalyst.
Tandem Hydrosilylation/o-C-H Silylation of Arylalkynes Catalyzed by Ruthenium Bis(silyl) Aminophosphine Complexes
Kitano, Takeo,Komuro, Takashi,Ono, Rikima,Tobita, Hiromi
, p. 2710 - 2713 (2017)
An unprecedented reaction via consecutive trans-selective hydrosilylation and o-C-H silylation of arylalkynes with hydrosilanes was developed by use of ruthenium complex catalysts Ru{?°3(Si,O,Si)-xantsil}(CO)(PR3) (R = NC4H8 (1-Pyrr), NC5H10 (1-Pip); xantsil = (9,9-dimethylxanthene-4,5-diyl)bis(dimethylsilyl)). This reaction proceeded with gentle heating at 40-60 °C and afforded novel 2,α-bis-silylated (Z)-stilbene or (Z)-styrene derivatives 2 together with an equimolar amount of (E)-/(Z)-arylalkenes as byproducts. The selectivity of the formation of 2 reached a maximum by employing catalyst 1-Pyrr ligated by the less bulky triaminophosphine P(NC4H8)3 and hydrosilane HSiMe(OSiMe3)2 having moderately bulky and electron withdrawing substituents.
Convenient Synthesis of Cyclic Trithiocarbonates from 1,2- or 1,3-Dihaloalkanes and Sodium Trithiocarbonate in the Presence of Phase-Transfer Catalyst
Sugawara, Akira,Sato, Tsukasa,Sato, Ryu
, p. 339 - 341 (1989)
Cyclic trithiocarbonates, such as 1,3-dithiolane-2-thiones and 1,3-dithiane-2-thiones, were conveniently synthesized by treating 1,2- or 1,3-dihaloalkanes with sodium trithiocarbonate in the presence of a phase-transfer catalyst.
Heck reaction catalyzed by phospha-palladacycles in non-aqueous ionic liquids
Herrmann, Wolfgang A.,Boehm, Volker P.W.
, p. 141 - 145 (1999)
Phospha-palladacycles are among the most powerful palladium catalyst systems for the Heck reaction. We have shown the use of non-aqueous ionic liquids (NAILs) as an alternative to traditional molecular solvents for this reaction, with the phospha-palladacycle catalysts resulting in easy product separation, possible catalyst recycling and further increases in catalyst productivity. Preliminary results obtained with bromo- and chloro arenes are presented.
Manganese chloride-catalyzed cross-coupling and carbonylative cross- coupling of organostannanes with iodonium salts
Kang, Suk-Ku,Kim, Won-Yeob,Lee, Yong-Tack,Ahn, Sung-Ki,Kim, Jin-Chul
, p. 2131 - 2132 (1998)
The MnCl2-4H2O-catalyzed cross-coupling and carbonylative cross- coupling of organostannanes with hypervalent iodonium salts afforded biaryls and biaryl ketones, respectively.
Ring-opening metathesis polymerization based pore-size-selective functionalization of glycidyl methacrylate based monolithic media: Access to size-stable nanoparticles for ligand-free metal catalysis
Bandari, Rajendar,H?che, Thomas,Prager, Andrea,Dimberger, Klaus,Buchmeiser, Michael R.
, p. 4650 - 4658 (2010)
Monolithic polymeric supports have been prepared by electron-beam-triggered free-radical polymerization using a mixture of glycidyl methacrylate and trimethylolpropane triacrylate in 2-propanol, 1-dodecanol, and toluene. Under appropriate conditions, phase separation occurred, which resulted in the formation of a porous monolithic matrix that was characterized by large (convective) pores in the 30 μm range as well as pores of 7 nm were hydrolyzed by using poly(styrenesulfonic acid) (Mw = 69400 gmol-1, PDI = 2.4). The remaining epoxy groups inside pores of 2(PCy3) 2-(CHPh)]. These immobilized Ru-alkylidenes were further used for the surface modification of the small pores by a grafting approach. A series of monomers, that is, 7-oxanorborn-5-ene-2,3-dicarboxylic anhydride (3), norborn-5ene-2,3-dicarboxylic anhydride (4), N,N-di-2-pyridyl-7-oxanorborn-5- ene-2-carboxylic amide (5), N,N-di-2-pyridyl-norbom-5-ene-2-carboxamide (6), N[2-(dimethylamino)ethyl]bicyclo-[2.2.1]hept-5-ene-2-carboxamide (7), and dimethyl bicyclo[2.2.1]hept-5-en-2-ylphosphonate (8), were used for this purpose. Finally, monoliths functionalized with poly-5 graft polymers were used to permanently immobilize Pd2+ and Pt4+, respectively, inside the pores. After reduction, metal nanoparticles 2nm in diameter were formed. The palladium-nanoparticle-loaded monoliths were used in both Heck- and Suzuki-type coupling reactions achieving turnover numbers of up to 167000 and 63000, respectively.
Palladium-catalyzed cross-coupling of triarylbismuth(V) derivatives with hypervalent iodonium salts
Kang,Ryu,Kim
, p. 1021 - 1026 (2001)
The palladium-catalyzed cross-coupling of hypervalent iodonium salts with organobismuth(V) derivatives was accomplished with PdCl2 (5 mol%) in CH3CN at room temperature.
Novel nickel nanoparticles stabilized by imidazolium-amidinate ligands for selective hydrogenation of alkynes
López-Vinasco, Angela M.,Martínez-Prieto, Luis M.,Asensio, Juan M.,Lecante, Pierre,Chaudret, Bruno,Cámpora, Juan,Van Leeuwen, Piet W. N. M.
, p. 342 - 350 (2020)
The main challenge in the hydrogenation of alkynes into (E)- or (Z)-alkenes is to control the selective formation of the alkene, avoiding the over-reduction to the corresponding alkane. In addition, the preparation of recoverable and reusable catalysts is of high interest. In this work, we report novel nickel nanoparticles (Ni NPs) stabilized by three different imidazolium-amidinate ligands (ICy·(Ar)NCN; L1: Ar = p-tol, L2: Ar = p-anisyl and L3: Ar = p-ClC6H4). The as-prepared Ni NPs were fully characterized by (HR)-TEM, XRD, WASX, XPS and VSM. The nanocatalysts are active in the hydrogenation of various substrates. They present a remarkable selectivity in the hydrogenation of alkynes towards (Z)-alkenes, particularly in the hydrogenation of 3-hexyne into (Z)-3-hexene under mild reaction conditions (room temperature, 3% mol Ni and 1 bar H2). The catalytic behaviour of Ni NPs was influenced by the electron donor/acceptor groups (-Me, -OMe, -Cl) in the N-aryl substituents of the amidinate moiety of the ligands. Due to the magnetic character of the Ni NPs, recycling experiments were successfully performed after decantation in the presence of an external magnet, which allowed us to recover and reuse these catalysts at least 3 times preserving both activity and chemoselectivity.
Fluoride-promoted cross-coupling of chloro(mono-, di-, or triphenyl)germanes with aryl halides in "moist" toluene. Multiple transfer of the phenyl group from organogermane substrates and comparison of the coupling efficiencies of chloro(phenyl)germanes with their corresponding stannane and silane counterparts
Pitteloud, Jean-Philippe,Zhang, Zun-Ting,Liang, Yong,Cabrera, Laura,Wnuk, Stanislaw F.
, p. 8199 - 8212 (2010)
The trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylgermanes undergo Pd-catalyzed cross-couplings with aryl bromides and iodides in the presence of tetrabutylammonium fluoride in toluene with addition of the measured amount of water. One chloride ligand on the Ge center allows efficient activation by fluoride to promote transfer of one, two, or three phenyl groups from the organogermanes. The corresponding chlorophenylstannanes were found to be more reactive than chlorophenylsilanes, which in turn were more effective than chlorophenylgermanes. One chloride ligand on the Ge or Si center allows efficient activation by fluoride to promote transfer of up to three aryl groups from germane or silicon. However, no haloligand was necessary to be present on the Sn center, since tetraphenyltin efficiently transferred up to four phenyl groups during fluoride-promoted couplings with aryl halides. 19F NMR studies suggested formation of the fluorophenylgermanes and the hypervalent germanate species as possible intermediates.
