17595-86-7Relevant articles and documents
Fast Suzuki-Miyaura cross-coupling reaction with hexacationic triarylphosphine Bn-dendriphos as ligand
Snelders, Dennis J. M.,Kreiter, Robert,Firet, Judith J.,Van Koten, Gerard,Gebbink, Robertus J. M. Klein
, p. 262 - 266 (2008)
The application of hexa[(dimethylamino)-methyl]-functionalized triphenylphosphine (1) and its benzylammonium salt, Bn-Dendriphos (2), in the Suzuki-Miyaura cross-coupling of aryl bromides with arylboronic acids is described. The 3,5-bis[(benzyldimethylammonio)methyl] substitution pattern in 2 leads to a rate enhancement compared to both the non-ionic parent compound 1 and triphenylphospine (PPh3) itself. At the same time, the resulting catalytic species are stable towards palladium black formation, even at a phosphine/palladium ratio of 1. These observations are attributed to the presence of a total of six ammonium groups in the backbone of the phosphine ligand, which presumably leads to an unsaturated phosphine-palladium complex.
Effects of co-solvents on reactions run under micellar catalysis conditions
Gabriel, Christopher M.,Lee, Nicholas R.,Bigorne, Florence,Klumphu, Piyatida,Parmentier, Michael,Gallou, Fabrice,Lipshutz, Bruce H.
, p. 194 - 197 (2017)
The impact of varying percentages of an organic solvent added to reactions run in aqueous nanomicelles as the reaction medium has been investigated. Issues such as rates of reaction, percent conversion, and yield, as well as various practical aspects (e.g
Mild-Base-Promoted Arylation of (Hetero)Arenes with Anilines
Monzón, Diego M.,Santos, Tanausú,Pinacho-Crisóstomo,Martín, Víctor S.,Carrillo, Romen
, p. 325 - 333 (2018/01/15)
Transition metal-free radical arylation of heteroarenes is achieved at room temperature by simply adding aqueous sodium carbonate to a solution of the corresponding heteroarene and arenediazonium salt, which can even be formed in situ. Such an easy, inexpensive and mild methodology has been optimized and applied to the expeditious modification of interesting molecular cores like naphthylimide or bisthienylcyclopentenes.
A Structure-Activity Relationship Study of Bitopic N 6-Substituted Adenosine Derivatives as Biased Adenosine A1 Receptor Agonists
Aurelio, Luigi,Baltos, Jo-Anne,Ford, Leigh,Nguyen, Anh T. N.,J?rg, Manuela,Devine, Shane M.,Valant, Celine,White, Paul J.,Christopoulos, Arthur,May, Lauren T.,Scammells, Peter J.
, p. 2087 - 2103 (2018/03/21)
The adenosine A1 receptor (A1AR) is a potential novel therapeutic target for myocardial ischemia-reperfusion injury. However, to date, clinical translation of prototypical A1AR agonists has been hindered due to dose limiting adverse effects. Recently, we demonstrated that the biased bitopic agonist 1, consisting of an adenosine pharmacophore linked to an allosteric moiety, could stimulate cardioprotective A1AR signaling in the absence of unwanted bradycardia. Therefore, this study aimed to investigate the structure-activity relationship of compound 1 biased agonism. A series of novel derivatives of 1 were synthesized and pharmacologically profiled. Modifications were made to the orthosteric adenosine pharmacophore, linker, and allosteric 2-amino-3-benzoylthiophene pharmacophore to probe the structure-activity relationships, particularly in terms of biased signaling, as well as A1AR activity and subtype selectivity. Collectively, our findings demonstrate that the allosteric moiety, particularly the 4-(trifluoromethyl)phenyl substituent of the thiophene scaffold, is important in conferring bitopic ligand bias at the A1AR.
