82777-09-1Relevant articles and documents
Synthesis of diiodinated biphenyls and iodinated meta-terphenyls by regioselective Suzuki-Miyaura cross-coupling reactions of 5-substituted 1,2,3-triiodobenzenes
Al-Zoubi, Raed M.,Al-Jammal, Walid K.,El-Khateeb, Mohammad Y.,McDonald, Robert
, p. 3374 - 3384 (2015)
A variety of 2,3-diiodinated biphenyl and iodinated meta-terphenyl derivatives were synthesized by a regioselective Suzuki-Miyaura cross-coupling reaction of 5-substituted 1,2,3-triiodobenzenes. By using 1 equiv. of arylboronic acid, the Suzuki-Miyaura re
Synthesis and Acidity of 5-(m-Terphenyl-2′-yl)-1 H-tetrazoles: Evidence for an Enhanced Polar-πEffect Compared to Carboxylic Acids
Bookser, Brett C.,Do, Quyen-Quyen,Sritana-Anant, Yongsak,Baldridge, Kim K.,Siegel, Jay S.
, p. 3197 - 3203 (2021)
The polar-πeffect on tetrazoles, medicinal chemistry isosteres of carboxylate, is tested by a Hammett pKa (microtitration) analysis over a series of 5-(m-terphenyl-2′-yl)-1H-tetrazoles. A comparison with m-terphenyl-2′-yl-carboxylic acids supports the isostere analogy also in response to environmental changes. Computational (B97D/def2TZVPPD) extension of the series plus a scan of solvents (vacuum to water) demonstrates the trend with the dielectric constant. The effect is energetically small but may make statistically significant contributions to the tetrazole pharmacological profile.
Efficient Suppression of Chain Transfer and Branching via Cs-Type Shielding in a Neutral Nickel(II) Catalyst
Wang, Chaoqun,Kang, Xiaohui,Dai, Shengyu,Cui, Fengchao,Li, Yunqi,Mu, Hongliang,Mecking, Stefan,Jian, Zhongbao
supporting information, p. 4018 - 4022 (2020/12/25)
An effective shielding of both apical positions of a neutral NiII active site is achieved by dibenzosuberyl groups, both attached via the same donors’ N-aryl group in a Cs-type arrangement. The key aniline building block is accessibl
ORGANIC ELECTROLUMINESCENCE DEVICE AND MONOAMINE COMPOUND FOR ORGANIC ELECTROLUMINESCENCE DEVICE
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Paragraph 0098-0100, (2020/06/16)
An organic electroluminescence device including a monoamine compound represented by the following Formula 1 in at least one of a plurality of organic layers, and a monoamine compound represented by the following Formula 1 are provided. The monoamine compo
Ir-catalyzed synthesis of substituted tribenzosilepins by dehydrogenative C-H/Si-H coupling
Shibata, Takanori,Uno, Ninna,Sasaki, Tomoya,Takano, Hideaki,Sato, Tatsuki,Kanyiva, Kyalo Stephen
, p. 3426 - 3432 (2018/04/14)
The Ir-catalyzed intramolecular reaction of 2′,6′-diaryl-2-(hydrosilyl)biphenyls gave substituted tribenzosilepins by direct dehydrogenative C-H/Si-H coupling. This is the first example of catalytic construction of the tribenzosilepin skeleton. Enantiomer
Synthesis of α-alkylated γ-butyrolactones with concomitant anhydride kinetic resolution using a sulfamide-based catalyst
Claveau, Romain,Twamley, Brendan,Connon, Stephen J.
supporting information, p. 7574 - 7578 (2018/11/02)
The Kinetic Resolution (KR) of α-alkylated enolisable disubstituted anhydrides has been shown to be possible for the first time. In the presence of an ad hoc designed novel class of bifunctional sulfamide organocatalyst, a regio-, diastereo- and enantioselective cycloaddition reaction between the enolisable anhydride and benzaldehydes provides densely functionalised γ-butyrolactones in one pot (up to 19:1 dr, 94% ee) with control over three contiguous stereocentres. The concomitant resolution of the starting material anhydride, provides access to a range of chiral succinate derivatives with selectivity factors up to S? = 10.5.
From bis(silylene) and bis(germylene) pincer-type nickel(II) complexes to isolable intermediates of the nickel-catalyzed sonogashira cross-coupling reaction
Gallego, Daniel,Brueck, Andreas,Irran, Elisabeth,Meier, Florian,Kaupp, Martin,Driess, Matthias,Hartwig, John F.
, p. 15617 - 15626 (2013/11/06)
The first [ECE]Ni(II) pincer complexes with E = SiII and E = GeII metallylene donor arms were synthesized via C-X (X = H, Br) oxidative addition, starting from the corresponding [EC(X)E] ligands. These novel complexes were fully characterized (NMR, MS, and XRD) and used as catalyst for Ni-catalyzed Sonogashira reactions. These catalysts allowed detailed information on the elementary steps of this catalytic reaction (transmetalation → oxidative addition → reductive elimination), resulting in the isolation and characterization of an unexpected intermediate in the transmetalation step. This complex, {[ECE]Ni acetylide → CuBr} contains both nickel and copper, with the copper bound to the alkyne π-system. Consistent with these unusual structural features, DFT calculations of the {[ECE]Ni acetylide → CuBr} intermediates revealed an unusual E-Cu-Ni three-center-two-electron bonding scheme. The results reveal a general reaction mechanism for the Ni-based Sonogashira coupling and broaden the application of metallylenes as strong σ-donor ligands for catalytic transformations.
Two efficient routes to m-terphenyls from 1,3-dichlorobenzenes
Saednya, Akbar,Hart, Harold
, p. 1455 - 1458 (2007/10/03)
In the first route 2,6-dichlorophenyllithium (5), prepared by direct lithiation of 1,3-dichlorobenzene, reacted with aryl Grignard reagents to give m-terphenyls in 57-93% yields; the methodology was extended to substituted 1,3-dichlorobenzenes (i.e. 8 → 10). Also, reaction of 5 with MgCl2 gave 2,6-dichlorophenyl-magnesium chloride which, on warming, produced the self-capture product tetrachloro-m-terphenyl 7 in moderate yield. In the second route, reaction of 1,3-dichlorobenzene with excess of aryllithium in diethyl ether at room temperature gave the corresponding m-terphenyls in 59-94% yields. Examples are given in which the aryllithium was prepared by three different routes (ArX + Li, ArX + t-BuLi, ArH + BuLi).
A One-Pot Synthesis of m-Terphenyls via a Two-Aryne Sequence
Du, Chi-Jen Frank,Hart, Harold,Ng, Kwok-Keung Daniel
, p. 3162 - 3165 (2007/10/02)
Aryl-Grignards (3+ equiv) react with 2,6-dibromoiodobenzene or other 1,2,3-trihalobenzenes to give 2,6-diarylphenylmagnesium halides.The mechanism involves Grignard exchange at the central halogen, followed by two cycles of magnesium halide loss and regioselective capture of the resulting aryne by the aryl-Grignard reagent (Scheme I).Typical examples are shown in Table I.The method is especially applicable to m-terphenyls in which the "outer" rings are identical and/or in which substitution at the 2' or other positions of the "central" ring is desired.
Syntheses and Spectral Properties of several Branched-chain Polyphenyls containing 1,2,3-Trisubstituted Ring(s)
Ozasa, Shigeru,Fujioka, Yasuhiro,Kikutake, Jun-ichiro,Ibuki, Eiichi
, p. 1572 - 1581 (2007/10/02)
Nine polyphenyls, including six new compound, 3'-phenyl-o-quaterphenyl (3), 2,6-diphenyl-m- (4), 2,6-diphenyl-p-terphenyl (5), 2,6,5'-triphenyl-m-terphenyl (6), 2',2''-diphenyl-m-quaterphenyl (8), and 2'-(phenyl-d5)-m-terphenyl (9), were synthesized by the Ullmann coupling reaction of aryl iodide(s) or by the Karash-type coupling reaction of deuterated aryl Grignard reagent with aryl iodide catalyzed by bis(acetylacetonato)-nickel(II).Infrared studies of the polyphenyls showed that the range 730-770 cm-1, generally accepted as the position of the C-H out-of-plane bending bands of phenyl rings, should be widened slightly to 730-781 cm-1.The high frequency bands were found to be correlated closely to the sterically overcrowded structure of terminal rings.Proton magnetic resonance spectral studies indicated that the characteristic spectral features of the polyphenyls containing 1,2,3-trisubstituted ring(s) were fully consistent with their conformational aspects deduced from stereomodels.Ultraviolet spectral data suggeted that the most probable conformation of the highly crowded 3',6''-diphenyl-o-quaterphenyl (1) is one in which the interplanar angles of the pivot bonds between the 1,2,3-trisubstituted ring and three benzene rings are rather smaller than those of the less crowded 2'-phenyl-m-terphenyl (2).Keywords - Ullmann reaction; nickel-complex-catalyzed cross-coupling; quaterphenyl; deuterated quaterphenyl; quinquephenyl; sexiphenyl; polyphenyl; IR; UV; 1H-NMR
