10540-36-0Relevant articles and documents
Suzuki-Miyaura reaction catalyzed by graphene oxide supported palladium nanoparticles
Shang, Ningzhao,Feng, Cheng,Zhang, Haiyan,Gao, Shutao,Tang, Ranxiao,Wang, Chun,Wang, Zhi
, p. 111 - 115 (2013)
Pd supported on polyamine modified graphene oxide (GO-NH 2-Pd2 +) was fabricated for the first time. The prepared catalyst was characterized by transmission electron microscopy, X-ray diffraction spectroscopy, X-ray photoelectron spectroscopy and infrared spectroscopy. The catalytic activity of the prepared catalyst was investigated by employing Suzuki-Miyaura coupling reaction as a model reaction. A series of biphenyl compounds were synthesized through the Suzuki-Miyaura reaction using GO-NH2-Pd2 + as catalyst. The yields of the products were in the range from 71% to 95%. The catalyst can be readily recovered and reused at least 10 consecutive cycles without significant loss its catalytic activity.
Discovery of a potent inhibitor of the antiapoptotic protein Bcl-X L from NMR and parallel synthesis
Petros, Andrew M.,Dinges, Jurgen,Augeri, David J.,Baumeister, Steven A.,Betebenner, David A.,Bures, Mark G.,Elmore, Steven W.,Hajduk, Philip J.,Joseph, Mary K.,Landis, Shelley K.,Nettesheim, David G.,Rosenberg, Saul H.,Shen, Wang,Thomas, Sheela,Wang, Xilu,Zanze, Irini,Zhang, Haichao,Fesik, Stephen W.
, p. 656 - 663 (2006)
The antiapoptotic proteins Bcl-xL and Bcl-2 play key roles in the maintenance of normal cellular homeostasis. However, their overexpression can lead to oncogenic transformation and is responsible for drug resistance in certain types of cancer. This makes Bcl-xL, and Bcl-2 attractive targets for the development of potential anticancer agents, Here we describe the structure-based discovery of a potent Bcl-xL inhibitor directed at a hydrophobic groove on the surface of the protein. This groove represents the binding site for BH3 peptides from proapoptotic Bcl-2 family members such as Bak and Bad. Application of NMR-based screening yielded an initial biaryl acid with an affinity (Kd) of ～300 μM for the protein. Following the classical "SAR by NMR" approach, a second-site ligand was identified that bound proximal to the first-site ligand in the hydrophobic groove. From NMR-based structural studies and parallel synthesis, a potent ligand was obtained, which binds to Bcl-xL with an inhibition constant (K i) of 36 ± 2 nM.
A general palladium-catalyzed cross-coupling of aryl fluorides and organotitanium (IV) reagents
He, Xiao-Yun
, p. 823 - 832 (2021/07/19)
Pd(OAc)2/1-[2-(di-tert-butylphosphanyl)phenyl]-4-methoxy-piperidine was demonstrated to effectively catalyze cross-coupling of aryl fluoride and aryl(alkyl) titanium reagent. Both electron-deficient and electron-rich aryl fluoride can react effectively with nucleophile and provide extensive functional groups tolerance. 2-Arylated product was realized by selective activation of the C–F bond. Graphic abstract: [Figure not available: see fulltext.].
Potassium trimethylsilanolate enables rapid, homogeneous suzuki-miyaura cross-coupling of boronic esters
Delaney, Connor P.,Kassel, Vincent M.,Denmark, Scott E.
, p. 73 - 80 (2019/12/24)
Herein, a mild and operationally simple method for the Suzuki-Miyaura cross-coupling of boronic esters is described. Central to this advance is the use of the organic-soluble base, potassium trimethylsilanolate, which allows for a homogeneous, anhydrous cross-coupling. The coupling proceeds at a rapid rate, often furnishing products in quantitative yield in less than 5 min. By applying this method, a >10-fold decrease in reaction time was observed for three published reactions which required >48 h to reach satisfactory conversion.
Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions
Gribanov, Pavel S.,Golenko, Yulia D.,Topchiy, Maxim A.,Minaeva, Lidiya I.,Asachenko, Andrey F.,Nechaev, Mikhail S.
, p. 120 - 125 (2018/01/17)
Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille cross-coupling, and one-pot, two-step stannylation/Stille cross-coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 [Pd(OAc)2/PCy3] under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes the SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls in a one-pot two-step procedure.
Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes
Lian, Chang,Yue, Guanglu,Zhang, Haonan,Wei, Liyan,Liu, Danyang,Liu, Sichen,Fang, Huayi,Qiu, Di
, p. 4019 - 4023 (2018/10/04)
A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.
Palladium-Catalyzed Cross-Coupling of Unactivated Aryl Sulfides with Arylzinc Reagents under Mild Conditions
Otsuka, Shinya,Fujino, Daishi,Murakami, Kei,Yorimitsu, Hideki,Osuka, Atsuhiro
supporting information, p. 13146 - 13149 (2016/02/19)
Cross-coupling of general aryl alkyl sulfides with arylzinc reagents proceeds smoothly, even at room temperature or below, with a palladium-N-heterocyclic carbene (NHC) catalyst. When combined with reactions that are unique to organosulfurs, that is, the SNAr sulfanylation or Pummerer reaction, the cross-coupling offers interesting transformations that are otherwise difficult to achieve. An alkylsulfanyl group is preferentially converted whilst leaving the tosyloxy and chloro intact, which expands the variety of orthogonal cross-coupling.
A convenient chemical-microbial method for developing fluorinated pharmaceuticals
Bright, Tara V.,Dalton, Fay,Elder, Victoria L.,Murphy, Cormac D.,O'Connor, Neil K.,Sandford, Graham
, p. 1135 - 1142 (2013/03/28)
A significant proportion of pharmaceuticals are fluorinated and selecting the site of fluorine incorporation can be an important beneficial part a drug development process. Here we describe initial experiments aimed at the development of a general method of selecting optimum sites on pro-drug molecules for fluorination, so that metabolic stability may be improved. Several model biphenyl derivatives were transformed by the fungus Cunninghamella elegans and the bacterium Streptomyces griseus, both of which contain cytochromes P450 that mimic oxidation processes in vivo, so that the site of oxidation could be determined. Subsequently, fluorinated biphenyl derivatives were synthesised using appropriate Suzuki-Miyaura coupling reactions, positioning the fluorine atom at the pre-determined site of microbial oxidation; the fluorinated biphenyl derivatives were incubated with the microorganisms and the degree of oxidation assessed. Biphenyl-4-carboxylic acid was transformed completely to 4′-hydroxybiphenyl-4-carboxylic acid by C. elegans but, in contrast, the 4′-fluoro-analogue remained untransformed exemplifying the microbial oxidation-chemical fluorination concept. 2′-Fluoro- and 3′-fluoro-biphenyl-4-carboxylic acid were also transformed, but more slowly than the non-fluorinated biphenyl carboxylic acid derivative. Thus, it is possible to design compounds in an iterative fashion with a longer metabolic half-life by identifying the sites that are most easily oxidised by in vitro methods and subsequent fluorination without recourse to extensive animal studies.
Room temperature palladium-catalyzed cross coupling of aryltrimethylammonium triflates with aryl grignard reagents
Reeves, Jonathan T.,Fandrick, Daniel R.,Tan, Zhulin,Song, Jinhua J.,Lee, Heewon,Yee, Nathan K.,Senanayake, Chris H.
supporting information; experimental part, p. 4388 - 4391 (2010/11/17)
Figure Presented. Aryltrimethylammonium triflates and tetrafluoroborates were found to be highly reactive electrophiles in the Pd-catalyzed cross coupling with aryl Grignard reagents. The coupling reactions proceed at ambient temperature with a nearly stoichiometric quantity of Grignard reagent, and diverse functionality is tolerated. Competition experiments established the reactivity of PhNMe3OTf relative to PhCl, PhBr, PhI, and PhOTf.
Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same
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Page/Page column 20, (2009/04/24)
In one embodiment of the present invention, a silicon-based cross-coupling reagent is disclosed which is a highly stable tetraorganosilicon compound allowing for a cross-coupling reaction under mild reaction conditions without using fluoride ions, transition metal promoter, or strong bases, and the residue of the silicon reagent can be recovered and reused. The silicon-based cross-coupling reagent is a silicon compound in which an o-hydroxymethylphenyl group is connected to a silicon atom for intramolecular activation.
