Application of 2,6-Diisopropylanilinide Lithium in Catalytic Hydroboration of Imine and Borane
A technology based on propylaniline 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 results. Universal applicability, short response time, simple and controllable response
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Embodiment 1
[0022] Example 1: 2,6-Diisopropylanilide Lithium catalyzes the hydroboration reaction of benzidine and pinacol borane
[0023] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylidene aniline under argon protection, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 40.9 ul of 2,6 - Tetrahydrofuran solution (0.6115M) of diisopropylanilinide lithium (5 mol% dosage, the same below), after reacting for 1 h, draw a drop into the NMR tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 96%. 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).
Embodiment 2
[0024] Example 2: 2,6-diisopropylanilide lithium catalyzed hydroboration reaction of benzidine and pinacol borane
[0025] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylidene aniline under argon protection, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 40.9 ul of 2,6 - Tetrahydrofuran solution (0.6115M) of diisopropylanilinide lithium (5 mol% dosage), after reacting for 2 h, draw a drop into the nuclear magnetic tube with a dropper, 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).
[0026] Replacing lithium 2,6-diisopropylanilide with the lithium amidide compound of formula I failed to obtain the product.
[0027]
Embodiment 3
[0028] Example 3: 2,6-Diisopropylanilide Lithium Catalyzed Hydroboration Reaction of Bianidine and Pinacol Borane
[0029] In the reaction flask that has been dehydrated and deoxygenated, add 0.5 mmol of benzylidene aniline under the protection of argon, add 100ul THF, then add 0.6 mmol (0.0871 mL) borane with a pipette and mix well, and finally add 32.7 ul of 2,6 - Tetrahydrofuran solution (0.6115M) of lithium diisopropylanilinide (4 mol% dosage), after reacting for 2 h, draw a drop into the nuclear magnetic tube with a dropper, add CDCl 3 Dubbed into a solution. Calculated 1 H spectrum yield was 97%. 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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