A kind of carboxylic acid deoxyboration hydroboration reaction method
A technology for hydroboration and carboxylic acid is applied in the field of catalytic reaction of magnesium metal compounds to achieve the effects of low catalyst dosage, simple structure and high reaction efficiency
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Embodiment 1
[0024] Large sterically hindered aminomagnesium alkyl compounds catalyze the synthesis of boronate compounds from benzoic acid and borane:
[0025] Under anhydrous and oxygen-free conditions, under the protection of nitrogen, in a glove box, add 0.25 mmol of benzoic acid into a Schlenk reaction flask with a stirring bar, then add 1.0 mmol of pinacol borane and mix well, and finally add a catalyst with a large space 0.00025 mmol of magnesium alkyl compounds stabilized by hindered amino ligands, stirred and reacted at 60°C for 1 hour, briefly pumped under the vacuum pump, and added CDCl 3 Measure NMR. Calculated 1 H spectrum yield 99%. NMR data of the main product: 1 H NMR (600MHz, CDCl 3 ): δ1.25 (s-overlap, 36H, CH 3 , OBpin&pinBOBpin), 4.91(s, 2H, OCH 2 ), 7.23-7.34 (m, 5H, ArH).
Embodiment 2
[0027] Large sterically hindered aminomagnesium alkyl compound catalyzes the synthesis of boronate compounds from p-toluic acid and borane:
[0028] Under anhydrous and oxygen-free conditions, under nitrogen protection, in a glove box, add 0.25 mmol of p-toluic acid to a Schlenk reaction flask with a stirring bar, then add 1.0 mmol of pinacol borane and mix well, and finally add the catalyst 0.00025 mmol of magnesium alkyl compound stabilized by large sterically hindered amino ligands, stirred and reacted at 60°C for 1 hour, briefly pumped under vacuum pump, and added CDCl 3 Measure NMR. Calculated 1 H spectrum yield 98%. NMR data of the main product: 1 H NMR (600MHz, CDCl 3 ): δ1.25 (s-overlap, 36H, CH 3 , OBpin&pinBOBpin), 2.32(s, 3H, ArCH 3 ), 4.87 (s, 2H, OCH 2 ), 7.12(d, 3 J HH =7.8Hz, 2H, ArH), 7.22(d, 3 J HH = 7.8 Hz, 2H, ArH).
Embodiment 3
[0030] Large sterically hindered aminomagnesium alkyl compound catalyzes the synthesis of boronate compounds from p-tert-butylbenzoic acid and borane:
[0031] Under anhydrous and oxygen-free conditions, under nitrogen protection, in a glove box, add 0.25 mmol of p-tert-butylbenzoic acid to a Schlenk reaction flask with a stirring bar, then add 1.0 mmol of pinacol borane and mix well, and finally add Catalyst 0.00025 mmol of magnesium alkyl compound stabilized by large sterically hindered amino ligand, stirred and reacted at 60°C for 1 hour, briefly pumped under vacuum pump, and added CDCl 3 Measure NMR. Calculated 1 H spectrum yield 99%. NMR data of the main product: 1 H NMR (600MHz, CDCl 3 ): δ1.26 (s-overlap, 36H, CH 3 , OBpin&pinBOBpin), 1.31(s, 9H, C(CH 3 ) 3 ), 4.89 (s, 2H, OCH 2 ), 7.27(d, 3 J HH = 8.4 Hz, 2H, ArH), 7.35 (m, 2H, ArH).
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