Application of 4-methoxyaniline lithium in catalysis of hydroboration reaction of imine and borane
A technology based on methoxyaniline and catalytic imine, which is applied in catalytic reactions, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of low yield of catalytic systems, long reaction time, expensive catalysts, etc., and achieve Good universality, short response time, simple and controllable effect
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Embodiment 1
[0023] Embodiment one: 4-methoxyanilinolithium catalyzes the hydroboration reaction of benzidine and pinacol borane
[0024] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, add 0.5 mmol of benzidine, add 100 ulTHF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 69.9 ul of 4-methanol Tetrahydrofuran solution (0.3577M) of lithium oxyanilinide (5 mol% dosage, the same below), after reacting for 1 h, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).
Embodiment 2
[0025] Example 2: 4-Methoxyanilino Lithium Catalyzed Hydroboration Reaction of Beniylidene Aniline and Pinacol Borane
[0026] In the reaction flask that has been dehydrated and deoxygenated, under the protection of argon, add 0.5 mmol of benzidine, add 100 ulTHF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 69.9 ul of 4-methanol Lithium oxyanilinide tetrahydrofuran solution (0.3577M) (5 mol% dosage), after 2 hours of reaction, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 99%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).
[0027] Substitution of the 4-methoxyanilinidelithium by the amide lithium compound of formula I did not yield the product.
[0028]
Embodiment 3
[0029] Example 3: 4-methoxyanilinolithium catalyzes the hydroboration reaction of benzidine and pinacol borane
[0030] In the dehydrated and deoxygenated reaction flask, under the protection of argon, add 0.5 mmol of aniline, add 100 ulTHF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 55.9 ul of 4-formazol Lithium oxyanilinide tetrahydrofuran solution (0.3577M) (4 mol% dosage), after reacting for 2 h, use a dropper to draw a drop into the NMR tube, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. NMR data of the product: 1 H NMR (CDCl 3 , 400MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).
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