1.Synthesis of N-(6-Arylbenzo[d]thiazole-2-acetamide Derivatives and Their Biological Activities: An Experimental and Computational Approach.
Gull Y1,2, Rasool N3, Noreen M4, Altaf AA5, Musharraf SG6, Zubair M7, Nasim FU8, Yaqoob A9, DeFeo V10, Zia-Ul-Haq M11. Molecules. 2016 Feb 25;21(3). pii: E266. doi: 10.3390/molecules21030266.
A new series of N-(6-arylbenzo[d]thiazol-2-yl)acetamides were synthesized by C-C coupling methodology in the presence of Pd(0) using various aryl boronic pinacol ester/acids. The newly synthesized compounds were evaluated for various biological activities like antioxidant, haemolytic, antibacterial and urease inhibition. In bioassays these compounds were found to have moderate to good activities. Among the tested biological activities screened these compounds displayed the most significant activity for urease inhibition. In urease inhibition, all compounds were found more active than the standard used. The compound N-(6-(p-tolyl)benzo[d]thiazol-2-yl)acetamide was found to be the most active. To understand this urease inhibition, molecular docking studies were performed. The in silico studies showed that these acetamide derivatives bind to the non-metallic active site of the urease enzyme. Structure-activity studies revealed that H-bonding of compounds with the enzyme is important for its inhibition.
2.Preparing (Multi)Fluoroarenes as Building Blocks for Synthesis: Nickel-Catalyzed Borylation of Polyfluoroarenes via C-F Bond Cleavage.
Zhou J1,2, Kuntze-Fechner MW2, Bertermann R2, Paul US2, Berthel JH2, Friedrich A2, Du Z1, Marder TB2, Radius U2. J Am Chem Soc. 2016 Apr 18. [Epub ahead of print]
The [Ni(IMes)2]-catalyzed transformation of fluoroarenes into arylboronic acid pinacol esters via C-F bond activation and transmetalation with bis(pinacolato)diboron (B2pin2) is reported. Various partially fluorinated arenes with different degrees of fluorination were converted into their corresponding boronate esters.
3.Alternating Intramolecular and Intermolecular Catalyst-Transfer Suzuki-Miyaura Condensation Polymerization: Synthesis of Boronate-Terminated π-Conjugated Polymers Using Excess Dibromo Monomers.
Nojima M1, Kosaka K1, Kato M1, Ohta Y1, Yokozawa T1. Macromol Rapid Commun. 2015 Oct 28. doi: 10.1002/marc.201500587. [Epub ahead of print]
The Suzuki-Miyaura coupling polymerization of dibromoarene 1 and arylenediboronic acid (ester) 2 with a Pd catalyst having a high propensity for intramolecular catalyst transfer is reported. The polymerization of excess 1 with 2 affords high-molecular-weight π-conjugated polymer having boronic acid (ester) moieties at both ends, contrary to Flory's principle. This unstoichiometric polycondensation behavior is accounted for by intramolecular transfer of the Pd catalyst on 1. In the polymerization of 1 and 2 having different aryl residues, high-molecular-weight polymer is obtained when the stronger donor aromatic is used as the dibromo monomer and the weaker donor or acceptor aromatic is used as diboronic acid (ester) monomer. The pinacol boronate moieties at both ends of the obtained poly(p-phenylene) (PPP) can be converted to benzoic acid ester, hydroxyl group, and bromine. Furthermore, the reaction of the pinacol boronate-terminated PPP with poly(3-hexylthiophene) (P3HT) having bromine at one end yields a triblock copolymer of P3HT-b-PPP-b-P3HT.
4.Low Bandgap Semiconducting Copolymer Nanoparticles by Suzuki Cross-Coupling Polymerization in Alcoholic Dispersed Media.
Parrenin L1,2,3, Brochon C1,2,3, Hadziioannou G1,2,3, Cloutet E1,2,3. Macromol Rapid Commun. 2015 Oct;36(20):1816-21. doi: 10.1002/marc.201500324. Epub 2015 Aug 21.
The synthesis and formulation of organic semiconductors for the emerging technology of organic electronics requires the use of preparative methods and solvents being environment friendly. Today most of the active layer materials for the organic photovoltaic devices and modules are using chlorinated solvents, which are toxic and hazardous. In this work, the synthesis of poly[N-9'-heptadecanyl-2,7-carbazole-alt-5,5-(4,7-di-2-thienyl-2',1',3'-benzothiadiazole] (PCDTBT) in propan-1-ol is presented as the dispersant continuous phase in the presence of poly(vinylpyrrolidone) used as stabilizer. Suzuki-Miyaura polycondensation of 9-(9-heptadecanyl)-9H-carbazole-2,7-diboronic acid bis(pinacol) ester and 4,7-bis(2-bromo-5-thienyl)-2,1,3-benzothiadiazole in alcohol dispersion yields colloidally stable nanoparticles of PCDTBT with particles size of 330-1300 nm, depending on the stabilizer concentration. Other reaction parameters are also discussed such as the amount of base or Pd catalyst.