13238-38-5Relevant academic research and scientific papers
"Click" dendrimer-stabilized palladium nanoparticles as a green catalyst down to parts per million for efficient C-C cross-coupling reactions and reduction of 4-nitrophenol
Deraedt, Christophe,Salmon, Lionel,Astruc, Didier
, p. 2525 - 2538 (2014)
The concept of the nanoreactor valuably contributes to catalytic applications of supramolecular chemistry. Therewith molecular engineering may lead to organic transformations that minimize the amount of metal catalyst to reach the efficiency of enzymatic catalysis. The design of the dendritic nanoreactor proposed here involves hydrophilic triethylene glycol (TEG) termini for solubilization in water and water/ethanol mixed solvents combined with a hydrophobic dendritic interior containing 1,2,3-triazole ligands that provide smooth stabilization of very small (1 to 2nm) palladium nanoparticles (PdNPs). The PdNPs stabilized in such nanoreactors are extraordinarily active in water/ethanol (1/1) for the catalysis of various carbon-carbon coupling reactions (Suzuki-Miyaura, Heck and Sonogashira) of aryl halides down to sub-ppm levels for the Suzuki-Miyaura coupling of aryl iodides and aryl bromides. The reduction of 4-nitrophenol to 4-aminophenol in water also gives very impressive results. The difference of reactivity between the two distinct dendrimers with, respectively, 27 (G0) and 81 (G1) TEG termini is assigned to the difference of PdNP core size, the smaller G0 PdNP core being more reactive than the G1 PdNP core (1.4 vs. 2.7nm), which is also in agreement with the leaching mechanism.
A versatile and efficient palladium-meta-terarylphosphine catalyst for the copper-free sonogashira coupling of (hetero-)aryl chlorides and alkynes
Yang, Yong,Chew, Xinying,Johannes, Charles W.,Robins, Edward G.,Jong, Howard,Lim, Yee Hwee
, p. 7184 - 7192 (2014)
A novel meta-terarylphosphine ligand, CyPhine, was developed and found to be a highly active promoter of copper-free Sonogashira cross-coupling reactions when combined in situ with a palladium source. The evolutionary m-terarylphosphine ligand architectur
Dialyzable carbosilane dendrimers as soluble supports for the functionalization of pyridine fragments via palladium-catalyzed coupling reactions
Le Notre, Jerome,Firet, Judith J.,Sliedregt, Leo A. J. M.,Van Steen, Bart J.,Van Koten, Gerard,Gebbink, Robertus J. M. Klein
, p. 363 - 366 (2005)
(Chemical Equation Presented) The use of carbosilane (CS) dendrimers as soluble supports in liquid phase organic synthesis (LPOS) is described. Control of the three key steps is perfectly achieved by covalently binding a pyridine fragment to the soluble s
Synthesis of symmetrical and unsymmetrical diarylalkynes from propiolic acid using palladium-catalyzed decarboxylative coupling
Park, Kyungho,Bae, Goun,Moon, Jeongju,Choe, Jaehoon,Song, Kwang Ho,Lee, Sunwoo
, p. 6244 - 6251 (2010)
Figure presented. Symmetrical diarylalkynes were obtained from propiolic acid (or 2-butynedioic acid) and aryl halides in good yields. The optimized reaction conditions were 2.0 equiv of aryl halide, 1.0 equiv of propiolic acid, 5.0 mol % Pd(PPh3/su
MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex as a highly efficient and recyclable catalyst for the Sonogashira reaction
Zhao, Hong,Huang, Bin,Wu, Yichao,Cai, Mingzhong
, p. 21 - 28 (2015)
Abstract A novel MCM-41-immobilized Schiff base-pyridine bidentate copper(I) complex [MCM-41-Sb,Py-CuI] was conveniently prepared from commercially available and inexpensive 3-aminopropyltriethoxysilane via immobilization on MCM-41, followed by reacting w
Catalytic alkynylation coupling reactions by copper(II) complex in water and its applications to domino synthesis of 2-arylindoles
Yu, Lintao,Jiang, Xiaofei,Wang, Lixia,Li, Zhengkai,Wu, Di,Zhou, Xiangge
, p. 5560 - 5562 (2010)
A mild and clean protocol for the alkynylation coupling of aryl iodides with terminal alkynes has been developed in yields up to 99% in the presence of sulfonato-CuII(salen) in water. Domino synthesis of 2-arylindoles from 2-iodoaniline and aryl acetylene was successfully carried out by this catalytic system, and the catalyst could be easily recovered and reused. A mild and clean protocol for the alkynylation coupling of aryl iodides with terminal alkynes has been developed in yields up to 99% in the presence of sulfonato-CuII(salen) in water. Domino synthesis of2-arylindoles from 2-iodoaniline and aryl acetylene was successfully carried out by this catalytic system. The catalyst can be easily recovered and reused.
Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents
Messa, Francesco,Dilauro, Giuseppe,Perna, Filippo M.,Vitale, Paola,Capriati, Vito,Salomone, Antonio
, p. 1979 - 1984 (2020)
The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.
Metal scavenging and catalysis by periodic mesoporous organosilicas with 2,2′-bipyridine metal chelating ligands
Waki, Minoru,Inagaki, Shinji
, (2021)
A periodic mesoporous organosilica containing 2,2′-bipyridine (BPy-PMO) was assessed as a metal scavenger and heterogeneous catalyst. The functionalized PMO was synthesized based on a modified version of a previously reported procedure and showed a large
Palladium-phosphinous acid-catalyzed Sonogashira cross-coupling reactions in water
Wolf, Christian,Lerebours, Rachel
, p. 2161 - 2164 (2004)
A palladium-phosphinous acid-catalyzed Sonogashira cross-coupling reaction that proceeds in water under air atmosphere in the absence of organic co-solvents has been developed. Disubstituted alkynes have been prepared in up to 91% yield by POPd-catalyzed
Alkynyl?B(dan)s in Various Palladium-Catalyzed Carbon?Carbon Bond-Forming Reactions Leading to Internal Alkynes, 1,4-Enynes, Ynones, and Multiply Substituted Alkenes
Tani, Tomohiro,Sawatsugawa, Yuuki,Sano, Yusuke,Hirataka, Yo,Takahashi, Naomi,Hashimoto, Sadahiro,Sugiura, Tetsuya,Tsuchimoto, Teruhisa
, p. 1815 - 1834 (2019)
It was found that the C(sp)?B(dan) bond of alkynyl?B(dan)s can be directly used for palladium-catalyzed carbon?carbon bond-forming reactions with aryl(alkenyl) halides and allylic carbonates as electrophiles, thus delivering unsymmetrical internal alkynes and unconjugated 1,4-enynes, respectively. With acyl chlorides as electrophiles, ynone synthesis is also promoted by a palladium catalyst with the assistance of a copper co-catalyst. These reactions can be achieved as more convenient one-pot reactions, without isolating the alkynyl?B(dan) formed in situ by the zinc-catalyzed dehydrogenative borylation of alkynes with HB(dan). In addition to direct C(sp)?B(dan) bond transformations, the C≡C bond in an alkynyl?B(dan) proved to be a promising scaffold for the construction of a multisubstituted alkene, which is synthesized by diboration of the C≡C?B(dan) moiety, leading to a triborylalkene followed by iterative regio- and stereoselective Suzuki?Miyaura cross-coupling reactions. As one example, the synthesis of the ethene with four different aryl groups, p-MeC6H4, p-MeOC6H4, p-NCC6H4, and p-F3CC6H4, was attained in high overall yield of 64% in six steps starting from the terminal alkyne, p-MeC6H4C≡CH. Besides these synthetic applications of the alkynyl?B(dan), the scope of the alkynyl substrate in the zinc-catalyzed dehydrogenative borylation was expanded to enhance the reliability as a provider of the alkynyl?B(dan). Consequently, 42 alkynes were found to participate in the dehydrogenative borylation as substrates; these are alkyl-, alkenyl-, aryl-, heteroaryl-, ferrocenyl-, silyl-, and borylalkynes, with or without a variety of functional groups. Lastly, a new method for preparing HB(dan), as a sulfide-free, cost-saving, and reaction-time-saving route, is disclosed. (Figure presented.).
