Application of phosphinate ligands in synthesis of fluorescent dye intermediate through olefin hydroformylation

Abstract

The invention discloses an application of a class of phosphinate ligands in synthesis of a fluorescent dye intermediate through olefin hydroformylation. The application comprises the following steps: S1, sequentially adding 0.001 mmol of Rh(acac)(CO)2, 0.0005 mmol of bidentate phosphinate ligands, P / Rh in a ratio of 1 / 1, 1 mmol of olefin and 1 mL of solvent toluene into a reaction flask, putting the reaction bottle into a high-pressure reaction kettle, and putting the high-pressure reaction kettle into a constant-temperature oil bath pan; and S2, transferring the mixed solution into a 25mL glass bottle added with 200 microliters of n-tridecane as an internal standard by using a rubber head dropper, and cleaning a reaction kettle for three times by using a certain amount of dichloromethane. The hydroformylation reaction of various olefins is catalyzed by the catalyst composed of rhodium / bidentate phosphinate, the chemical selectivity of the product aldehyde is high, and the sum of the molar ratio of the product aldehyde to isomerized olefin to alkane is 88-100%.

Description

technical field [0001] The present invention relates to the application field of a class of phosphinate ligands in the synthesis of fluorescent dye intermediates by hydroformylation of olefins, in particular to the synthesis of fluorescent dye intermediates by a class of phosphinate ligands in the hydroformylation of olefins in the application. Background technique [0002] Since the development of the hydroformylation reaction, there have been many reports aimed at solving the chemical / regioselectivity of the product aldehyde, mainly in the design and synthesis of a series of phosphine ligands with different electronic / steric hindrance effects to solve this problem, but through the second There are not many reports on the regulation of transition metal-catalyzed olefin hydroformylation by phosphonate ligands, and the catalytic effect of the "transition metal-phosphinate" catalysts is not good. The existing bidentate phosphinic acid The hydroformylation reaction of alkenes ...

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Problems solved by technology

[0002] Since the development of the hydroformylation reaction, there have been many reports aimed at solving the chemical / regioselectivity of the product aldehyde, mainly in the design and synthesis of a series of phosphine ligands with different electronic / steric hindrance effects to solve this problem, but through the second There are not many reports on the regulation of transition metal-catalyzed olefin hydroformylation by phosphonate ligands, and the catalytic effect of the "transition metal-phosphinate" catalysts is not good. The existing bidentate phosphinic acid The hydroformylation reaction of alkenes catalyzed by ester ligands regulated by rhodium catalysts is less universal. Ester ligand-regulated rhodium catalysts catalyze the hydroformylation of 2,5-cyclohexadiene substrates, which have special structures and are not universal

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