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Polysubstituted ethylene compound as well as preparation method and application thereof
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A compound, multi-substitution technology, applied in the field of chemistry, can solve the problems of difficult separation, poor control of double bond configuration, etc.
Active Publication Date: 2020-12-08
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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Among them, for the coupling involving transition metals, the oxidative addition of aryl halides, the transmetallation of arylboron reagents, arylmetal reagents and transition metals, and the activation of C-H bonds mediated by directing groups, etc. Form metal aryl species, and then carry out alkyneintercalation reaction with metal aryl species and alkyne compounds or perform Heck reaction with 1,1-disubstituted alkenes and 1,2-disubstituted alkenes to obtain multi-substituted vinyl compounds, but The configuration of the double bond is not easy to control
For multi-substituted vinyl compounds, Z / E isomers are often of similar polarity and difficult to separate
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Embodiment 1
[0126] Synthesis of compound 3aa:
[0127]
[0128] In the dry Schlenk tube, under argon protection, add 3.4mg Pd(OAc) 2 , 10.6mg P(2-OMe-Ph) 3 , 78mg 1aa (0.3mmol), 133mg 2aa (0.9mmol), 141mg CsOPiv, 3mL THF, heated to 110°C, stirred for 3h. Quench the reaction with 5 mL of saturated ammoniumchlorideaqueous solution, extract three times with 5 mL of ethyl acetate, wash the organic phase with saturated NaCl solution, dry over anhydroussodiumsulfate, concentrate, and use n-hexane as eluent for column chromatography to collect the product band. 73.0 mg of 3aa white solid was obtained with a yield of 95%.
[0129] 1 H NMR (400MHz, CDCl 3 )δ7.37–7.25(m,8H),7.23–7.18(m,2H),7.16–7.07(m,3H),7.05–6.99(m,2H),6.96(s,1H).
Embodiment 2
[0131] Synthesis of compound 3ab:
[0132]
[0133] Using 1ab as raw material, refer to Example 1 for the operation, and the yield is 74%.
[0134] 1 H NMR (400MHz, CDCl 3 )δ7.36–7.26(m,5H),7.22(t,J=7.4Hz,1H),7.17–7.09(m,4H),7.03(dd,J=13.9,5.5Hz,4H),6.94(s ,1H), 2.30(s,3H); EI-MS m / z(%): 270(M+).
Embodiment 3
[0136] Synthesis of compound 3ac:
[0137]
[0138] Using lac as raw material, refer to Example 1 for the operation, and the yield is 72%.
[0139] 1 H NMR (400MHz, CDCl 3 )δ7.35–7.26(m,5H),7.17–7.02(m,9H),6.92(s,1H),2.38(s,3H); EI-MS m / z(%):270(M+).
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Abstract
The invention discloses a polysubstituted ethylene compound as well as a preparation method and application thereof. The invention particularly discloses a preparation method of a polysubstituted ethylene compound as shown in a formula III, which comprises the following step: in an organic solvent, carrying out reaction as shown in the specification on a compound as shown in a formula I and a compound as shown in a formula II in the presence of a palladium catalyst, a phosphine ligand and alkali to obtain the polysubstituted ethylene compound as shown in the formula III. The preparation methodcan be suitable for various types of substrates, and the configuration of double bonds is controllable.
Description
technical field [0001] The invention relates to the field of chemistry, in particular to a multi-substituted vinyl compound, its preparation method and application. Background technique [0002] Substituted vinyl compounds widely exist in natural products, active drug intermediates and luminescent materials. Among them, the polyaryl-substituted vinyl backbone has been widely studied due to its aggregation-induced emission (AIE) effect. In 2001, Tang's research group discovered for the first time the aggregation-induced luminescent properties of silole compounds. Subsequently, cyano-substituted toluene (CN-BPE), triphenylethylene (TriPE), and tetraphenylethylene (TPE) compounds have been deeply researched due to their simple and stable molecular structure, convenient synthesis steps and significant AIE effect. Research. [0003] [0004] In 2002, Park et al. (J.Am.Chem.Soc., 2002,124,14410.) found that 1-cyano-trans-1,2-bis(4-methylbiphenyl)ethylene (CN -MBE) has an ag...
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