28446-70-0Relevant articles and documents
Pd-Catalyzed desulfitative arylation of olefins by: N -methoxysulfonamide
Ojha, Subhadra,Panda, Niranjan
supporting information, p. 1292 - 1298 (2022/02/19)
A novel Pd-catalyzed protocol for the desulfitative Heck-type reaction of N-methoxy aryl sulfonamides with alkenes was reported. The cross-coupling reaction was performed successfully with a variety of olefins to obtain aryl alkenes. Different substituents on the aromatic ring of N-methoxysulfonamides were also found to be compatible with the reaction conditions. Expectedly, the reaction proceeds through CuCl2-promoted generation of the nitrogen radical and subsequent desulfonylation under thermal conditions to afford the aryl radical for the Pd-catalyzed coupling reaction. N-Methoxysulfonamide was further exploited for the synthesis of symmetrical biaryls in the presence of CuCl2. This journal is
Selective α-Deuteration of Cinnamonitriles using D2O as Deuterium Source
Guo, Beibei,de Vries, Johannes G.,Otten, Edwin
supporting information, p. 179 - 186 (2021/10/12)
The selective α-deuteration of α,β-unsaturated nitriles using the strong base tBuOK or a metal-ligand cooperative Ru pincer catalyst is described. With D2O as deuterium source and glyme as solvent at 70 °C, tBuOK is an efficient catalyst for deuteration at the α-C(sp2) position of cinnamonitriles, providing access to a broad range of deuterated derivatives in good to excellent yields and with very high levels of deuterium incorporation. While the tBuOK-catalysed protocol does not tolerate base-sensitive functional groups, cinnamonitrile derivatives containing a benzylic bromide or ester moiety were deuterated in excellent yields using Milstein's ruthenium PNN pincer catalyst. Moreover, the activity for H/D exchange of the metal-ligand cooperative Ru catalyst is found to be significantly higher than that of tBuOK, allowing reactions to proceed well even at room temperature. A mechanistic proposal is put forward that involves deprotonation of the cinnamonitrile α-CH position when using tBuOK as catalyst, whereas H/D exchange catalysis with the Ru PNN pincer likely proceeds via (reversible) oxa-Michael addition of D2O. (Figure presented.).
Cu-catalyzed cyanomethylation of imines and α,β-alkenes with acetonitrile and its derivatives
Ahmad, Muhammad Siddique,Ahmad, Atique
, p. 5427 - 5431 (2021/02/12)
We describe copper-catalyzed cyanomethylation of imines and α,β-alkenes with a methylnitrile source and provide an efficient route to synthesize arylacrylonitriles and β,γ-unsaturated nitriles. This method tolerates aliphatic and aromatic alkenes substituted with a variety of functional groups such as F, Cl, Br, Me, OMe,tert-Bu, NO2, NH2and CO2H with good to excellent yields (69-98%). These systems consist of inexpensive, simple copper catalyst and acetonitrile with its derivatives (α-bromo/α-iodo-acetonitrile) and are highly applicable in the industrial production of acrylonitriles.
8-Hydroxyquinolin-2(1H)-one analogues as potential β2-agonists: Design, synthesis and activity study
Xing, Gang,Zhi, Zhengxing,Yi, Ce,Zou, Jitian,Jing, Xuefeng,Yiu-Ho Woo, Anthony,Lin, Bin,Pan, Li,Zhang, Yuyang,Cheng, Maosheng
, (2021/07/19)
β2-Agonists that bind to plasmalemmal β2-adrenoceptors causing cAMP accumulation are widely used as bronchodilators in chronic respiratory diseases. Here, we designed and synthesized a group of 8-hydroxyquinolin-2(1H)-one analogues and studied their β2-agonistic activities with a cellular cAMP assay. Compounds B05 and C08 were identified as potent (EC50 2-agonists among the compounds tested. They behaved as partial β2-agonists in non-overexpressed HEK293 cells, and possessed rapid smooth muscle relaxant actions and long duration of action in isolated guinea pig tracheal strip preparations. In summary, B05 and C08 are β2-agonists with potential applicability in chronic respiratory diseases.
A new palladium heterogeneous complex (Pd-Gu@BOEH): chemoselective, phosphine-free and practical nanocatalyst in carbon–carbon cross-coupling reaction
Jafari, Fariba,Ghorbani-Choghamarani, Arash,Hasanzadeh, Neda
, p. 1033 - 1049 (2020/11/05)
Herein, boehmite nanoparticles were synthesized via combination of Al(NO3)3·9H2O and NaOH in aqueous solution. This nanomaterial converted to Pd-Gu@BOEH in several sequences. Pd-Gu@BOEH was used as efficient and recoverable nanocatalyst for the chemoselective C–C band formation such as Mizoroki–Heck and Suzuki–Miyaura reactions without any phosphine ligands or inert atmosphere. This catalyst has been characterized by several analyses such as EDS, WDX, SEM, XRD, FT-IR, TEM, TGA, AAS and BET. Also, obtained products from C–C coupling reactions were identified by NMR spectroscopy and their melting points. This catalyst was recycled in described reactions without palladium leaching. The reused catalyst was characterized by EDS, WDX, XRD, FT-IR and AAS analysis, which showed good stability during reaction process.
Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction
Ye, Runyou,Zhu, Maoshuai,Yan, Xufei,Long, Yang,Xia, Ying,Zhou, Xiangge
, p. 8678 - 8683 (2021/07/26)
A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.
Manganese(I)-Catalyzed H-P Bond Activation via Metal-Ligand Cooperation
Pérez, Juana M.,Postolache, Roxana,Casti?eira Reis, Marta,Sinnema, Esther G.,Vargová, Denisa,De Vries, Folkert,Otten, Edwin,Ge, Luo,Harutyunyan, Syuzanna R.
supporting information, p. 20071 - 20076 (2021/12/03)
Here we report that chiral Mn(I) complexes are capable of H-P bond activation. This activation mode enables a general method for the hydrophosphination of internal and terminal α,β-unsaturated nitriles. Metal-ligand cooperation, a strategy previously not considered for catalytic H-P bond activation, is at the base of the mechanistic action of the Mn(I)-based catalyst. Our computational studies support a stepwise mechanism for the hydrophosphination and provide insight into the origin of the enantioselectivity.
Design, synthesis and biological evaluation of 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one derivatives as potent β2-adrenoceptor agonists
Yi, Ce,Xing, Gang,Wang, Siqi,Li, Xiaoran,Liu, Yichuang,Li, Jinyan,Lin, Bin,Woo, Anthony Yiu-Ho,Zhang, Yuyang,Pan, Li,Cheng, Maosheng
, (2019/11/26)
A series of β2-adrenoceptor agonists with an 8-(2-amino-1-hydroxyethyl)-6-hydroxy-1,4-benzoxazine-3(4H)-one moiety is presented. The stimulatory effects of the compounds on human β2-adrenoceptor and β1-adrenoceptor were characterized by a cell-based assay. Their smooth muscle relaxant activities were tested on isolated guinea pig trachea. Most of the compounds were found to be potent and selective agonists of the β2-adrenoceptor. One of the compounds, (R)-18c, possessed a strong β2-adrenoceptor agonistic effect with an EC50 value of 24 pM. It produced a full and potent airway smooth muscle relaxant effect same as olodaterol. Its onset of action was 3.5 min and its duration of action was more than 12 h in an in vitro guinea pig trachea model of bronchodilation. These results suggest that (R)-18c is a potential candidate for long-acting β2-AR agonists.
Pd–ninhydrin immobilized on magnetic nanoparticles: synthesis, characterization, and application as a highly efficient and recoverable catalyst for Suzuki–Miyaura and Heck–Mizoroki C–C coupling reactions
Hajjami, Maryam,Shirvandi, Zeinab
, p. 1059 - 1072 (2020/01/06)
Abstract: In this work by controlling the interaction between the inorganic complexes and the support material, we have designed a high-activity nanostructured combined of magnetic nanoparticles and Pd–ninhydrin-terminated complex as catalyst. The as-prepared catalyst was characterized by FT-IR, XRD, VSM, SEM, EDAX, ICP, and TGA techniques. This magnetic nanostructure can be used as a novel, green, and efficient heterogeneous catalyst for Suzuki–Miyaura and Heck–Mizoroki C–C coupling reactions. This catalyst showed promising catalytic activity and excellent yields toward various aryliodides and arylbromides in mild reaction conditions. In Suzuki–Miyaura reactions, various aryl halides (I, Br) were coupled with phenyl boronic acids in 5?mg of catalyst and 8?mg of catalyst used for Mizoroki–Heck reaction of aryl halides (I, Br) with n-butyl acrylate or acrylonitrile. The catalyst was reusable and recycled six times without a significant loss in activity and leaching of palladium. Graphic abstract: [Figure not available: see fulltext.].
Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones
Gorbunova, Yelizaveta,Zakusilo, Dmitriy N.,Boyarskaya, Irina A.,Vasilyev, Aleksander V.
, (2020/05/25)
Reactions of 3-arylpropenenitriles [ArCH[dbnd]CHCN] with arenes [Ar'H] under the superelectrophilic activation conditions with Br?nsted superacid TfOH (CF3SO3H) or strong Lewis acid AlBr3 result, first, in the formation of products of hydroarylation of the carbon-carbon double bond, 3,3-diarylpropanenitriles [Ar(Ar’)CHCH2CN]. Reactions may go further in TfOH leading to 3-arylindanones, as products of intramolecular aromatic acylation by the electrophilically activated nitrile group. Intermediate cationic species, derived at the protonation of the starting 3-arylpropenenitriles onto the carbon of C[dbnd]C bond and the nitrile nitrogen, have been studied by DFT calculation. A plausible reaction mechanism including the formation of highly reactive dications [(Ar)HC+–CH2C+ = NH] has been proposed. The obtained 3,3-diarylpropanenitriles have been transformed into pharmaceutically valuable 5-(2,2-diarylethyl)-1H-tetrazoles [Ar(Ar’)CHCH2Tetr] and 3-diarylpropylamines [Ar(Ar’)CH(CH2)2NH2] by the reactions with NaN3 and LiAlH4 correspondingly.
