Copper catalyzed cross-coupling reactions of diaryl ditellurides with potassium aryltrifluoroborate salts

We present here results of the cross-coupling reaction of diaryl ditellurides with potassium aryltrifluoroborate salts using a catalytic amount of Cu(OAc)2 and bypiridine in DMSO/H2O under air atmosphere. This cross-coupling reaction is general and was performed with diaryl ditellurides and potassium aryltrifluoroborate salts bearing electron-withdrawing, electron-donating and neutral substituents, affording the corresponding unsymmetrical diaryl tellurides in good to excellent yields.Apresentamos aqui resultados das reações de acoplamento de diteluretos de diarila com sais de ariltrifluoroborato de potássio, usando quantidades catalíticas de Cu(OAc)2 e bipiridina, em uma mistura de DMSO/H2O, sob ar atmosférico. Estas reações de acoplamento são gerais e são realizadas com diteluretos de diarila e sais de ariltrifluoroborato de potássio contendo substituintes neutros, retiradores e doadores de elétrons, fornecendo os correspondentes teluretos de diarila não simétricos em rendimentos de bons a excelentes.Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP) (Grants 07/56659-0 and 07/59404-2

Crystallographic, DFT and docking (cathepsin B) studies on an organotellurium(IV) compound

Some biologically active organotellurium compounds exhibit inhibitory potency against cathepsin B. In this study, an alkyl derivative, viz. [CH3(CH2)2C(I)=C(H)](nBu)TeI2, 1, has been structurally characterised by X-ray crystallography and shown to be coordinated within a C2I2 donor set. When the stereochemically active lone pair of electrons is taken into account, a distorted trigonal bipyramidal geometry results with the iodide atoms in axial positions. Both intra- and inter-molecular Te···I interactions are also noted. If all interactions are considered, the coordination geometry is based on a Ψ-pentagonal bipyramidal geometry. An unusual feature of the structure is the curving of the functionalised C5 chain. This feature has been explored by DFT methods and shown to arise as a result of close C–H···I interactions. A docking study (cathepsin B) was performed to understand the inhibition mechanism and to compare the new results with previous observations. Notably, 1 has the same pose exhibited by analogous biologically active compounds with aryl groups. Thus, the present study suggests that (alkyl)2TeX2 compounds should also be evaluated for biological activity

Potassium trifluoro­[(Z)-3-methoxy­prop-1-en­yl]borate

In the title salt, K+·C4H7BF3O−, the K atom is surrounded by six anions making close contacts through seven F [K⋯F = 2.779 (1)–3.048 (1) Å] and two O [K⋯O = 2.953 (2) and 3.127 (2) Å] atoms in a trivacant fac-vIC-9 icosa­hedral coordination geometry

Potassium trifluoro­[(Z)-3-(oxan-2-yl­oxy)prop-1-en-1-yl]borate monohydrate

The title compound, K+·C8H13BF3O2 −·H2O, which was obtained from the reaction of a modified form of Z-vinylic telluride via a transmetalation reaction with n-BuLi, crystallizes as K+ and C8H13BF3O2 − ions along with a water mol­ecule. The K+ cation is surrounded by four anions, making close contacts with six F atoms at 2.659 (3)–2.906 (3) Å and with two O atoms at 2.806 (3) and 2.921 (3) Å in a distorted bicapped trigonal-prismatic geometry

Dammarane Triterpenoids from Carnauba, Copernicia prunifera (Miller) H. E. Moore (Arecaceae), Wax

Phytochemical investigation from carnauba (Copernicia prunifera) wax led to the identification of sixteen dammarane-type triterpenes, including thirteen new characterized as: (24R*)-methyldammara-20,25-dien-3 alpha-ol and a mixture of alkyl (24R*)-methyldammar-25-en- 20-ol-3 beta-carboxylates, together with three previously described triterpenes: carnaubadiol, (24R*)-methyldammara-20,25-dien-3 beta-ol and (24R*)-24-methyldammara-20,25-dien-3-one. Moreover, four fatty alcohols (eicosanol, docosanol, tetracosanol and hexacosanol) as well as four sterols (cholesterol, campesterol, stigmasterol, and sitosterol) were also obtained. These compounds were isolated using classical chromatographic methods and their structures were determined by spectroscopic and chemical methods.Univ Fed Piaui, Dept Quim, BR-64049550 Teresina, PI, BrazilUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, BrazilUniv Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210180 Santo Andre, SP, BrazilUniv Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP, BrazilWeb of Scienc

Nucleophilic addition of potassium organotrifluoroborates to chiral cyclic N-acyliminium ions: stereoselective synthesis of functionalized N-heterocycles

The stereoselective nucleophilic addition of potassium aryl- and alkynyltrifluoroborates to cyclic N-acyliminium ion derivatives from N-benzyl-3,4,5-triacetoxy-2-pyrrolidinone, affording the respective 5-substituted 2-pyrrolidinone is described. The products were obtained in moderate to good yields and with preference for the syn diastereomer. (C) 2008 Elsevier Ltd. All rights reserved

Crystal and molecular structures of dichloro((Z)-2-chloro-2-phenylvinyl)(organo)tellurium(IV) for organo = n-butyl and phenyl

In each of the title compounds, R[Ph(Cl)C=(H)C]TeCl(2), R = nBu (1) and Ph (2), the primary geometry about the Te(IV) atom is a pseudo-trigonal-bipyramidal arrangement, with two Cl atoms in apical positions, and the lone pair of electrons and C atoms in the equatorial plane. As the Te(IV) is involved in two, an intra- and an inter-molecular, Te center dot center dot center dot Cl interactions the coordination geometry might be considered as a Psi-pentagonal bipyramid in each case. In addition, in (2) there is a hint of a Te center dot center dot center dot pi interaction (Te center dot center dot center dot C = 3.911(3) A). The key feature in the crystal structure of both compounds is the formation of supramolecular chains mediated by Te center dot center dot center dot Cl contacts. (1): C(12)H(15)Cl(3)Te, triclinic, P (1) over bar, a = 5.9471 (11), b = 10.7826(22), c = 11.7983(19) angstrom, alpha = 75.416(12), beta = 78.868(13), gamma = 80.902(14)degrees, V = 713.6(2) angstrom(3), Z = 2, R(1) = 0.021; (2): C14HIIC13Te, orthorhombic, Pcab, a=7.7189(10), b=17.415(2), c=21.568(3)angstrom, V = 2899.3(6) angstrom(3), Z = 8, R(1) = 0.027.FAPESPCNPqCAPE

Chemoselective cross-coupling Suzuki-Miyaura reaction of (Z)-(2-chlorovinyl)tellurides and potassium aryltrifluoroborate salts

An ultrasound-assisted synthesis of functionalized vinylic chlorides is described by palladium-catalyzed cross-coupling reaction of potassium aryltrifluoroborate salts and (Z)-2-chloro vinylic tellurides. This procedure offers easy access to vinylic chlorides architecture that contains sterically demanding groups in good yields. (C) 2008 Elsevier B.V. All rights reserved.Univ São Paulo, Fac Ciencias Farmaceut, Dept Farm, São Paulo, BrazilUniv São Paulo, Inst Quim, São Paulo, BrazilUniversidade Federal de São Paulo, Dept Biofis, São Paulo, BrazilUniversidade Federal de São Paulo, Dept Biofis, São Paulo, BrazilWeb of Scienc