Application of p-methylaniline lithium in catalysis of hydroboration reaction of imine and borane
A methylaniline-based, catalytic imine technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compound/hydride/coordination complex catalysts, etc., can solve the problem of low yield of the catalytic system and reaction time. long time, expensive catalysts, etc., to achieve the effect of wide substrate application range, short reaction time and good universality
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Embodiment 1
[0023] Example 1: Lithium p-methylanilide catalyzes the hydroboration reaction of benzidine and pinacol borane
[0024] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100 ulTHF, then add 0.5 mmol (0.0726 mL) borane with a pipette and mix well, and finally add 34.4 ul of p-methyl Tetrahydrofuran solution (0.7273M) of lithium anilide (5 mol% dosage, the same below), after reacting for 2 h, draw a drop into the NMR tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 91%. 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] Embodiment two: p-methylanilide lithium catalyzes the hydroboration reaction of benzidine and pinacol borane
[0026] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100 ulTHF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 34.4 ul of p-methyl Tetrahydrofuran solution (0.7273M) of lithium anilide (0.7273M) (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, 1H), 1.29 (s, 12H).
Embodiment 3
[0027] Example 3: Lithium p-methylanilide catalyzes the hydroboration reaction of benzidine and pinacol borane
[0028] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylaniline under the protection of argon, add 100 ulTHF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 34.4 ul of p-methyl Tetrahydrofuran solution (0.7273M) of lithium anilide (5 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 99%. NMR data of the product: 1 H NMR (CDCl 3 , 400 MHz) δ : 7.29~7.12(m, 9H), 6.88~6.84 (t, 1H), 4.69 (s, 2H), 1.29 (s, 12H).
[0029] Substitution of p-toluidelithium by the amide lithium compound of formula I did not yield the product.
[0030]
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