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Compounds and their applications in metathesis reactions
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A technology of metathesis reaction and compound, applied to compound and its application field in metathesis reaction, can solve problems such as difficulty in large-scale use
Active Publication Date: 2020-04-24
沃比奥联合生物能源公司
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Therefore, they may be difficult to use on a large scale in industrial production requiring larger quantities
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Embodiment 1
[0285] Embodiment 1: the synthesis of compound 2 . The 2ml benzene solution of TBS-Bitet-2-OH (115mg) was added dropwise to W(N-2,6-Cl 2 C 6 h 3 ) (CHCMe 3 )-(NC 4 (CH 3 ) 2 h 2 ) 2 (135mg) in benzene (2ml) solution. The reaction mixture was stirred at room temperature for 4 hours and the volatile materials were removed in vacuo. The residue was dissolved in DME (1,2-dimethoxyethane) (2 ml) and a portion of 1-methoxy-2-vinylbenzene (54.5 mg) in DME (2 ml) was added, followed by Stir for 4 hours. The reaction mixture was then concentrated in vacuo to give a dark red oil which was crystallized from n-pentane to give the desired product (91 mg). 1 H-NMR (200MHz, C 6 D. 6 ): δ-0.25(s, 3H), 0.24(s, 3H), 0.88(s, 9H), 1.31-2.49(m, 20H), 2.99-3.31(m, 4H), 3.67(s, 3H), 6.09-6.29(m, 4H), 6.48(t, J=8.2Hz, 1H), 6.60-6.73(m, 2H), 6.78-6.91(m, 3H), 7.28(s, 1H), 11.27(s, 1H).
Embodiment 2
[0286] Embodiment 2: the synthesis of compound 3 . W(N-2,6-Cl 2 C 6 h 3 ) (CHCMe 3 )-(NC 4 (CH 3 ) 2 h 2 ) 2 (100mg) in benzene (2ml) was added to a solution of 4Br-TPPOH (79mg) in benzene (2ml). The reaction mixture was stirred at room temperature for 4 hours and the volatile materials were removed in vacuo. The residue was dissolved in 2ml DME and a portion of 1-methoxy-2-vinylbenzene (45mg) in DME (2ml) was added and stirring was continued for a further 4 hours. The reaction mixture was then concentrated in vacuo to give a dark red oil which was crystallized from n-pentane to give the desired product (112 mg). 1H-NMR (200MHz, C 6 D. 6 ): δ1.87(s, 6H), 3.21(s, 3H), 5.88(s, 2H), 6.15-6.30(m, 2H), 6.42-6.61(m, 2H), 6.71-7.09(m, 20H ), 11.19(s, 3H).
Embodiment 3
[0287] Embodiment 3: the synthesis of compound 17 . Add 2ml of benzene solution of TBS-Bitet-2-OH (86mg) dropwise to W(N-2,6-Cl 2 C 6 h 3 ) (CHCMe 3 )-(NC 4 (CH 3 ) 2 h 2 ) 2 (100mg) in benzene (2ml) solution. The reaction mixture was stirred at room temperature for 4 hours and the volatile materials were removed in vacuo. The residue was dissolved in DME (2ml) and a portion of 1-(methoxymethyl)-2-vinylbenzene (45mg) in DME (2ml) was added and stirring continued for a further 4 hours. The reaction mixture was then concentrated in vacuo to give a dark red oil which was crystallized from n-pentane to give the desired product (12 mg). 1 H-NMR (200MHz, C 6 D. 6 ): δ-0.12(s, 3H), 0.21(s, 3H), 0.79(s, 9H), 1.16-1.64(m, 10H), 1.85-2.55(m, 14H), 3.19(s, 3H), 5.99-6.33 (m, 3H), 6.44-6.83 (m, 5H), 7.18-7.35 (m, 3H), 11.58 (s, 1H).
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Abstract
The present disclosure provides a Group 6 complex that, in some embodiments, can be used to catalyze olefin metathesis reactions. In some embodiments, the compound is a compound of the following formula (I), wherein: M is a Group 6 metal atom; X is an oxygen atom, =N-R 5 、=N‑N(R 5 )(R 5’ ) or =N‑O‑R 5 ,R 5 and R 5’ independently various substituents, such as aryl or heteroaryl, all of which are optionally substituted; n is 0 or 1; R z is a neutral ligand; R 1 is hydrogen or an organic substituent; R 2 is aryl or heteroaryl, both of which are optionally substituted; R 3 is an anionic ligand; and R 4 is an anionic ligand such as pyrrole, pyrazole, imidazole, indole, azindole or indazole, all optionally substituted.
Description
technical field [0001] The present invention generally discloses organometallic complexes and their use as catalyst compounds. In some embodiments, the organometallic complexes disclosed herein catalyze metathesis reactions between ethylenically unsaturated compounds. Background technique [0002] Alkene metathesis (olefin metathesis) is a reaction between alkene or alkene groups in which formally alkylene groups are exchanged between alkene or alkene groups. Examples of metathesis reactions include cross-decomposition, the reaction between two different alkenes to form one or more new alkenes, ring-opening reactions of cyclodienes which can be carried out under polymerization, ring-closing metathesis reactions of dienes, with internal alkenes The combination of double-bonded olefins forms olefins with terminal olefinic double bonds in the ethenolysis reaction, and from terminal olefins via homo-metathesis to form internal olefins. [0003] US2011 / 007742 generally disclose...
Claims
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