25871-69-6Relevant articles and documents
Convenient access to 1,3,5-triaroylbenzenes
Joseph, Delphine,Jankowski, Raphael,Prim, Damien,Mahuteau, Jacqueline,Chiaroni, Angèle
, p. 8051 - 8054 (2002)
The unusual transformation of β-aryl-β-haloacroleins into valuable triaroylbenzenes is reported by the first time. The convenient sequence takes advantage on the one step access to triaroylbenzenes. This work establishes that the presence of amine is required for the trimerization procedure since it is involved in the formation of iminium-enamine intermediate A.
Iron-catalyzed trimerization of terminal alkynes enabled by pyrimidinediimine ligands: A regioselective method for the synthesis of 1,3,5-substituted arenes
Doll, Julianna S.,Eichelmann, Robert,Hertwig, Leif E.,Bender, Thilo,Kohler, Vincenz J.,Bill, Eckhard,Wadepohl, Hubert,Ro?ca, Drago?-Adrian
, p. 5593 - 5600 (2021/05/31)
The development of pyrimidine-based analogues of the well-known pyridinediimine (PDI) iron complexes enables access to a functional-group-tolerant methodology for the catalytic trimerization of terminal aliphatic alkynes. Remarkably, in contrast to established alkyne trimerization protocols, the 1,3,5-substituted arenes are the main reaction products. Preliminary mechanistic investigations suggest that the enhanced π-acidity of the pyrimidine ring, combined with the hemilability of the imine groups coordinated to the iron center, facilitates this transformation. The entry point in the catalytic cycle is an isolable iron dinitrogen complex. The catalytic reaction proceeds via a 1,3-substituted metallacycle, which explains the observed 1,3,5-regioselectivity. Such a metallacycle could be isolated and represents a rare 1,3-substituted ferracycle obtained through alkyne cycloaddition.
Aromatic ketone compound and organic light-emitting device thereof
-
, (2020/03/12)
The invention provides an aromatic ketone compound and an organic light-emitting device. thereof, wherein the aromatic ketone compound has the structure (I) shown, in a formula shown in the description . X1 And X2 The lines are the s
Silver(I)-Promoted Radical Sulfonylation of Allyl/Propargyl Alcohols: Efficient Synthesis of γ-Keto Sulfones
Fang, Guichun,Liu, Jianquan,Shang, Weidong,Liu, Qun,Bi, Xihe
, p. 3334 - 3338 (2016/12/14)
An efficient Ag2CO3-promoted sulfonylation of allyl/propargyl alcohols with sodium sulfinates has been developed. The reaction tolerates a wide range of functional groups to deliver γ-keto sulfones in high yields (up to 93 %). Propargyl alcohols furnished trimerization product 1,3,5-triaroylbenzenes in the presence of sodium methanesulfinate under the standard conditions. A mechanism involving a sulfonyl radical was suggested.
Microporous, tetraarylethylene-based polymer networks generated in a reductive polyolefination process
Preis,Dong,Brunklaus,Scherf
supporting information, p. 1582 - 1587 (2015/04/27)
Microporous Polymer Networks (MPNs) that contain aggregate-induced emission (AIE) active tetraphenylethylene (TPE) or other tetraarylethylene units have been generated in a reductive polyolefination process starting from four different tris(α,α-dichlorobenzyl)arene derivatives with dicobalt octacarbonyl or chromium(ii)acetate as reductive olefination agents. Microporosity with moderately high BET surface areas up to 500 m2 g-1 could be combined with high solid state photoluminescence quantum yields up to 25.3% for polymer network P4. This unique combination should be promising for applications as optical solid state sensors, especially for MPNs with electron-deficient triazine core units.
Metal-free synthesis of 1,3,5-trisubstituted benzenes by the cyclotrimerization of enaminones or alkynes in water
Wan, Jie-Ping,Lin, Yunfang,Hu, Kaikai,Liu, Yunyun
, p. 20499 - 20505 (2014/06/09)
The cyclotrimerization reactions of enaminones and electron deficient terminal alkynes have been efficiently performed in water in the presence of only a small amount of lactic acid. The reactions led to the green synthesis of a variety of 1,3,5-triacylbenzenes without using any metal as catalyst. Brief investigation on different elaboration of the triacylbenzene product demonstrated the versatile synthetic application of these 1,3,5-triacylbenzenes. This journal is the Partner Organisations 2014.
Reactivity of the 16-electron CpCo half-sandwich complex containing a B(3,6)-disubstituted o-carborane-1,2-dithiolate ligand
Tang, Xiao,Wang, Zhaojin,Li, Yizhi,Yan, Hong
supporting information, p. 90 - 97 (2013/11/19)
The 16-electron (16e) half-sandwich complex CpCo(S2C 2B10H8)(CHCHCO2Me)2 (1; Cp = cyclopentadienyl) was considered as inert owing to hindered di-substitution at B sites. However in methanol complex 1 reacts with ethynylferrocene (FcCCH) and dimethyl acetylenedicarboxylate (DMAD, MeO2CCCCO2Me) to lead to two-fold alkyne insertion at Co-S bond to give rise to unusual stable 18e adduct CpCo(S2C2B10H8) (CHCHCO2Me)2(HCCFc)(MeO2CCCCO2Me) (2) containing mixed alkynes. Also in methanol complex 1 undergoes intramolecular hydrogen transfer of one CHCHCO2Me unit to adjacent carbon to form a CH2CCO2Me unit, thus producing the 18e complex CpCo(S2C2B10H8)[CH 2CCO2Me][CHCHCO2Me] (3). Further investigation indicates that complex 1 can catalyze [2 + 2 + 2] cycloaddition of alkynes. The catalytic efficiency is determined by temperature and nature of alkynes. In THF in the presence of [N(n-Bu)4]Br complex 1 is transformed to ionic complex [N(n-Bu)4]+[Co(S2C2B 10H8)2(CHCHCO2Me)4] - (4), in which metal-dithiolene is planar. Analogous [N(n-Bu) 4]+[Co(S2C2B10H 9)2(CHCHCO2Me)2]- (5) was also synthesized from mono-substituted precursor CpCo(S2C 2B10H9)(CHCHCO2Me) (1′). The electrochemical properties of both 4 and 5 show significant positive shift of redox peaks versus the analogous bis(1,2-benzenedithiolato)cobaltate (III) (Co(bdt)2). Reactivity of both neutral 16e CpCo complexes and ionic metal-dithiolene derivatives declines with the increase of substituents on carborane cage. All the new compounds have been characterized by NMR, IR, mass spectrometry, elemental analysis, and 2, 3, and 4 have been structurally characterized by X-ray diffraction.
Facile synthesis of 1,3,5-triaroylbenzenes by direct cyclotrimerization of ketone enolates
Liu, Feng-Shou,Liu, Xue-Hong,Ye, Kang-Zhi,Shen, Dong-Sheng
, p. 1640 - 1645 (2013/05/22)
Based on the improvement of the synthesis of 1,3,5-triaroylbenzenes, a convenient acid catalytic strategy was carried out and a series of 1,3,5-triaroylbenzenes were synthesized. The reaction temperature effect was investigated, and a mechanism of the cyclotrimerization has been proposed. Copyright Taylor & Francis Group, LLC.
Mechanistic and exploratory investigations into the synthesis of 1,3,5-triaroylbenzenes from 1-aryl-2-propyn-1-ones and 1,3,5-triacetylbenzene from 4-methoxy-3-buten-2-one by cyclotrimerization in hot water in the absence of added acid or base
Iwado, Tatsuya,Hasegawa, Keiya,Sato, Toshiyuki,Okada, Masaki,Sue, Kiwamu,Iwamura, Hiizu,Hiaki, Toshihiko
, p. 1949 - 1954 (2013/04/23)
Neat 1-phenyl- and 1-(p-tolyl)-2-propyn-1-ones (1 and 1′, respectively) were heated in water without any additive at 150 °C for 2 h to give 1,3,5-tribenzoyl- and 1,3,5-tri-(p-toluoyl)benzenes (2 and 2′, respectively) in 74 and 52% yields, respectively. The crossed reactions of 1 with the enolate of p-toluoylacetaldehyde (3′) and 1′ with the enolate of benzoylacetaldehyde (3) were carried out to give unsymmetrically substituted 1-toluoyl-3,5-dibenzoylbenzene (Ph2Tol) and 1,3-ditoluoyl-5-benzoylbenzene (PhTol2), respectively, corroborating the previously proposed reaction mechanism in which 3 and 3′ that are formed by rate-determining nucleophilic attack of HO- on 1 and 1′ or its conjugate acids formed by subsequent protonation would serve as a common intermediate for the formation of 2, 2′ and the acetophenone derivatives as byproducts. When 4-methoxy-3-buten-2-one (4) was heated in hot pure water without any additive at 150 °C for 30 min, 1,3,5-triacetylbenzene (5) was obtained in an isolated yield of 77% just by removing water by filtering the crystalline product from the cooled reaction mixture. The reaction did not take place in the absence of water. Slow decompositions of 5 in water set in at the temperature of 300 °C for 30 min.
Enantioselective construction of 2,5-dihydropyrrole skeleton with quaternary stereogenic center via catalytic asymmetric 1,3-dipolar cycloaddition involving α-arylglycine esters
Shi, Feng,Xing, Gui-Juan,Tan, Wei,Zhu, Ren-Yi,Tu, Shujiang
supporting information, p. 1482 - 1489 (2013/05/08)
A catalytic asymmetric construction of synthetically and biologically important 2,5-dihydropyrrole scaffolds with concomitant creation of multiple chiral carbon centers including one quaternary stereogenic center in high yields (up to 99%) and excellent e
