214360-69-7Relevant academic research and scientific papers
Dibenzo[d, d ′]benzo[2,1- b:3,4- b ′]difurans with extended π-conjugated chains: Synthetic approaches and properties
Hayasaka, Chikara,Hirano, Masafumi,Kiyota, Sayori,Komine, Nobuyuki,Nakano, Koji,Okada, Harumi
, p. 1003 - 1017 (2022/02/07)
Ru-catalysed cross-dimerisation of 3,8-di(hexyn-1-yl)dibenzo[d,d']benzo[2,1-b,3,4-b']difuran [3,8-di(hexyn-1-yl)-DBBDF] with 2 equivalents of methyl (E)-penta-2,4-dienoate produces 3,8-bis[(1E,3E,5E)-2-butyl-6-methoxycarbonylhexa-1,3,5-trien-1-yl]-DBBDF (9a), and the total yield of 9a obtained from 2,3-difluoro-1,4-diiodobenzene is 50% using the six-step reaction. A series of 3,8-bis(hexatrienyl)-DBBDF compounds and unsymmetrical 8-decyl-3-hexatrienyl-DBBDF compounds were also prepared using the same method. These compounds were evaluated using ultraviolet-visible (UV-vis) spectroscopy and cyclic voltammetry (CV). Time-dependent density-functional theory (TD-DFT) calculations indicate that efficient π-π? excitations occur using the conjugated trienyl side chain groups.
Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes
Wright, Jay S.,Sharninghausen, Liam S.,Preshlock, Sean,Brooks, Allen F.,Sanford, Melanie S.,Scott, Peter J. H.
supporting information, p. 6915 - 6921 (2021/05/29)
This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.
Amine-borane complexes: Air- and moisture-stable partners for palladium-catalyzed borylation of aryl bromides and chlorides
Guerrand, Hélène D. S.,Vaultier, Michel,Pinet, Sandra,Pucheault, Mathieu
, p. 1167 - 1174 (2015/04/22)
A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.
Unsaturated iridium pyridinedicarboxylate pincer complexes with catalytic activity in borylation of arenes
Hanh Nguyen, Duc,Perez-Torrente, Jesus J.,Lomba, Laura,Victoria Jimenez,Lahoz, Fernando J.,Oro, Luis A.
experimental part, p. 8429 - 8435 (2011/10/10)
Unsaturated σ,π-cyclooctenyl and hydrido Ir(iii) complexes bearing an unusual tridentate dianionic ONO pincer-type ligand have been straightforwardly obtained from 2,6-pyridinedicarboxylic acid and standard Ir(i) starting materials. These complexes efficiently catalyzed the arene C-H borylation under thermal conditions. The Royal Society of Chemistry 2011.
Iridium complexes of CCC-pincer N-heterocyclic carbene ligands: Synthesis and catalytic C-H functionalization
Chianese, Anthony R.,Mo, Allen,Lampland, Nicole L.,Swartz, Raymond L.,Bremer, Paul T.
experimental part, p. 3019 - 3026 (2010/10/03)
A series of four meta-phenylene-bridged bis-benzimidazolium chlorides were synthesized as precursors to rigid, monoanionic, CCC-pincer N-heterocyclic carbene ligands. For ligands with mesityl, 3,5-xylyl, or 3,5-di-tert-butylphenyl side groups, reaction with [Ir(1,5-cyclooctadiene)Cl]2 in acetonitrile with either excess triethylamine or stoichiometric cesium fluoride as base gave neutral, iridium(III) pincer complexes of the formula Ir(CCC)HCl(MeCN), which were purified by chromatography on silica gel. Metalation failed under these conditions for a 2,6-diisopropylphenyl-substituted derivative. In combination with NaOtBu, these complexes form active catalysts for the acceptorless dehydrogenation of cyclooctane and for arene C-H borylation in neat arene solvent.
Hydroboronation process
-
Page column 56, (2010/02/05)
The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.
Regioselective aromatic borylation in an inert solvent.
Tse,Cho,Smith 3rd.
, p. 2831 - 2833 (2007/10/03)
[reaction: see text]. A protocol for performing Rh catalyzed aromatic borylations in cyclohexane has been devised. Borylation at the 5-position of several 1,3-substituted aromatic species ranging from electron-rich (1,3-(NMe(2))(2)C(6)H(4)) to electron-deficient (1,3-(CF(3))(2)C(6)H(4)) yields the corresponding aryl boronate esters. Veratrole was selectively borylated at the 4-position, thus extending regioselectivity to 1,2-substituted benzenes. Selective borylation at the 3-position of an N-protected pyrrole has also been demonstrated, providing a valuable reagent for cross-coupling reactions in a single step.
