38262-85-0Relevant academic research and scientific papers
A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls
Hu, Rui,Li, Xinmin,Ren, Changyue,Yuan, Zeli,Zhang, Hang,Zhang, Tingting
supporting information, p. 4748 - 4753 (2020/08/17)
A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.
Palladium nanoparticles embedded in metal-organic framework derived porous carbon: Synthesis and application for efficient Suzuki-Miyaura coupling reactions
Dong, Wenhuan,Zhang, Li,Wang, Chenhuan,Feng, Cheng,Shang, Ningzhao,Gao, Shutao,Wang, Chun
, p. 37118 - 37123 (2016/05/24)
A nanoporous carbon (NPC) material was prepared by one-step direct carbonization of a metal-organic framework, MOF-5, without additional carbon precursors. Pd nanoparticles were immobilized on the MOF-5-derived NPC by an impregnation method coupled with subsequent reduction with NaBH4. The prepared catalyst was in-depth characterized by X-ray photoelectron spectroscopy, transmission electron microscopy, scanning electron microscopy, and N2 adsorption. The catalyst was used to catalyze the Suzuki-Miyaura coupling reactions and exhibited high catalytic efficiency with yields ranging from 90% to 99% under mild conditions. The results demonstrated the great application potential of MOF precursor-based metal nanoparticle composites in catalysis.
Site-Selective Iron(III) Chloride-Catalyzed Arylation of 4-Aryl-4-methoxy-2,5-cyclohexadienones for the Synthesis of Polyarylated Phenols
Sawama, Yoshinari,Masuda, Masahiro,Nakatani, Ryosuke,Yokoyama, Hiroki,Monguchi, Yasunari,Dohi, Toshifumi,Kita, Yasuyuki,Sajiki, Hironao
supporting information, p. 3683 - 3687 (2016/12/16)
The iron(III) chloride-catalyzed Friedel–Crafts arylation of 4-aryl-4-methoxy-2,5-cyclohexadienones, which were easily prepared by the phenyliodine(III) diacetate (PIDA)-mediated oxidation of 4-arylphenols in methanol, proceeded site-selectively to form meta-terphenyl (2,4-diarylphenol) derivatives in good yields. The subsequent PIDA-mediated oxidation and iron(III) chloride-catalyzed Friedel–Crafts arylation of the resulting products gave the corresponding 2,4,6-triarylphenol derivatives. The present method provides useful highly substituted polyarylated compounds. (Figure presented.).
Palladium-catalyzed direct arylation of phenols with aryl iodides
Long, Rongrong,Yan, Xufei,Wu, Zhiqing,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
supporting information, p. 3571 - 3574 (2015/03/30)
An efficient protocol of palladium-catalyzed direct para-arylation of unfunctionalized phenols with aryl iodides under mild conditions was reported. A variety of substrates were applied in this reaction with yields up to 87%.
Palladium nanoparticles in glycerol: A versatile catalytic system for C-X bond formation and hydrogenation processes
Chahdoura, Faouzi,Pradel, Christian,Gomez, Montserrat
supporting information, p. 3648 - 3660 (2014/01/06)
Palladium nanoparticles stabilised by tris(3-sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in C-X bond formation processes (X=C, N, P, S) and C-C multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as-prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular- and surface-like behaviour), has allowed attractive applications in one-pot multi-step transformations catalysed by palladium, such as C-C coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor. Copyright
Self-assembled poly(imidazole-palladium): Highly active, reusable catalyst at parts per million to parts per billion levels
Yamada, Yoichi M. A.,Sarkar, Shaheen M.,Uozumi, Yasuhiro
supporting information; experimental part, p. 3190 - 3198 (2012/04/10)
Metalloenzymes are essential proteins with vital activity that promote high-efficiency enzymatic reactions. To ensure catalytic activity, stability, and reusability for safe, nontoxic, sustainable chemistry, and green organic synthesis, it is important to develop metalloenzyme-inspired polymer-supported metal catalysts. Here, we present a highly active, reusable, self-assembled catalyst of poly(imidazole-acrylamide) and palladium species inspired by metalloenzymes and apply our convolution methodology to the preparation of polymeric metal catalysts. Thus, a metalloenzyme-inspired polymeric imidazole Pd catalyst (MEPI-Pd) was readily prepared by the coordinative convolution of (NH4)2PdCl4 and poly[(N-vinylimidazole)-co-(N- isopropylacrylamide)5] in a methanol-water solution at 80 °C for 30 min. SEM observation revealed that MEPI-Pd has a globular-aggregated, self-assembled structure. TEM observation and XPS and EDX analyses indicated that PdCl2 and Pd(0) nanoparticles were uniformly dispersed in MEPI-Pd. MEPI-Pd was utilized for the allylic arylation/alkenylation/vinylation of allylic esters and carbonates with aryl/alkenylboronic acids, vinylboronic acid esters, and tetraaryl borates. Even 0.8-40 mol ppm Pd of MEPI-Pd efficiently promoted allylic arylation/alkenylation/vinylation in alcohol and/or water with a catalytic turnover number (TON) of 20 000-1 250 000. Furthermore, MEPI-Pd efficiently promoted the Suzuki-Miyaura reaction of a variety of inactivated aryl chlorides as well as aryl bromides and iodides in water with a TON of up to 3 570 000. MEPI-Pd was reused for the allylic arylation and Suzuki-Miyaura reaction of an aryl chloride without loss of catalytic activity.
Negishi cross-coupling reaction catalyzed by an aliphatic, phosphine based pincer complex of palladium. biaryl formation via cationic pincer-type Pd IV intermediates
Gerber, Roman,Blacque, Olivier,Frech, Christian M.
experimental part, p. 8996 - 9003 (2011/10/31)
The aliphatic, phosphine-based pincer complex [(C10H 13-1,3-(CH2P(Cy2)2)Pd(Cl)] (1) is a highly active Negishi catalyst, enable to quantitatively couple various electronically activated, non-activated, deactivated, sterically hindered and functionalized aryl bromides with various diarylzinc reagents within short reaction times and low catalyst loadings. Experimental observations strongly indicate that a molecular mechanism is operative with initial chloride dissociation of 1 and formation of the cationic T-shaped 14e- complex [(C10H13-1,3-(CH2P(C6H 11)2)2)Pd]+ (B), which undergoes oxidative addition of an aryl bromide (Ar′Br) to yield the cationic, penta-coordinated aryl bromide pincer complexes of type [(C10H 13-1,3-(CH2P(Cy2)2)Pd(Br) (aryl′)]+ (C) with the metal center in the oxidation state of +IV and the aryl unit in cis position relative to the aliphatic pincer core. Subsequent transmetalation with Zn(aryl)2 result in the cationic diaryl pincer complexes of type [(C10H13-1,3-(CH 2P(Cy2)2)Pd(aryl)(aryl′)]+ (D), which reductively eliminate the coupling products, thereby regenerating the catalyst. The neutral square planar aryl pincer complex - a possible key intermediate in the catalytic cycle - was found to be reversibly formed in the reaction mixture but is not involved in the catalytic mechanism. Similarly, palladium nanoparticles as the catalytically active form of 1 could have been excluded. The Royal Society of Chemistry 2011.
[Pd(Cl)2(P(NC5H10)(C6H 11)2)2] - A highly effective and extremely versatile palladium-based negishi catalyst that efficiently and reliably operates at low catalyst loadings
Bolliger, Jeanne L.,Frech, Christian M.
experimental part, p. 11072 - 11081 (2010/11/16)
[Pd(Cl)2(P(NC5H10)-(C6H 11)2]2] (1) has been prepared in quantitative yield by reacting commercially available [Pd(cod)(Cl)2] (cod = cyclooctadiene) with readily prepared 1-(dicyclohexylphosphanyl)piperidine in toluene under N2 within a few minutes at room temperature. Complex 1 has proved to be an excellent Negishi catalyst, capable of quantitatively coupling a wide variety of electronically activated, non-activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100°C in the presence of just 0.01 mol% of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetais, lactones, amides, anilines, alkenes, carboxylic acids, acetic acids, and pyridines and pyrimidines, have been successfully used as coupling partners. Furthermore, electronic and steric variations are tolerated in both reaction partners. Experimental observations strongly indicate that a molecular mechanism is operative.
Desymmetrization of cyclohexadienones via bronsted acid-catalyzed enantioselective oxo-michael reaction
Gu, Qing,Rong, Zi-Qiang,Zheng, Chao,You, Shu-Li
supporting information; experimental part, p. 4056 - 4057 (2010/05/01)
Chemical Reaction Reprentation Desymmetrlzatlon of cyclohexadlenones via enantloselectlve oxo-Mlchael reaction catalyzed by chlral phosphoric add to afford highly enantloenrlched 1,4-dloxane and tetrahydrofuran derivatives In excellent yields has been realized. The newly established methodology allows the facile enantloselectlve synthesis of clerolndlclns C, D, and F.Copyright
