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Chiral rhodium complex and its uses as catalyst

The technology of a rhodium complex and a catalyst is applied to a chiral rhodium complex and its application field as a catalyst, and can solve the problems such as no report on chiral imidazoline salts, and achieve the effect of high catalytic efficiency

Inactive Publication Date: 2007-07-11
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Carbohydrates have a wide range of sources and rich stereochemistry, but their derived chiral imidazolinium salts have not been reported so far

Method used

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  • Chiral rhodium complex and its uses as catalyst
  • Chiral rhodium complex and its uses as catalyst
  • Chiral rhodium complex and its uses as catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] At 110°C, N,N'-bis(methyl 3-deoxy-4,6-O-benylidene-α-D-altropyranoside-3-yl)ethylenediamine (2.0g, 3.4mmol ), ammonium chloride (0.3g, 5.6mmol) was reacted in 40mL of triethyl orthoformate for 3-5 hours, cooled, filtered, and washed with petroleum ether to obtain 2.0g of product (92%); m.p.1 53-4°C ;[a] 20 D =+127.9 (c 1.0, ethanol). 1 H NMR (400MHz, CDCl 3 ): δ8.83(s, 1H), 7.40-7.15(m, 10H), 5.88(br, 2H), 5.50(s, 2H), 4.57(s, 2H), 4.30-4.05(m, 8H), 3.90(br, 2H), 3.75-3.60(m, 4H), 3.10(s, 6H), 3.06(s, 2H). 13 C NMR (100MHz, CDCl 3 ): δ157.29, 136.96, 129.44, 128.45(2C), 126.12(2C), 102.55, 100.70, 74.51, 69.30, 66.86, 58.66, 58.22, 55.43, 50.09. IR(KBr): 3440, 3257, 2930, 16 , 1459, 1409, 1262, 1138, 1104, 995, 964, 772, 707. MS (ESI) m / z (%): 599 [M + -Cl] (100).

Embodiment 2

[0026] At 45°C, the product obtained in Example 1 (1.35g, 2.15mmol), [RhCl(COD)] 2 (0.40g, 0.82mmol) and NaO t Bu (0.31g, 3.2mmol) was reacted in THF (20mL) for 48 hours, filtered and purified by column chromatography to obtain 1.06g product (77%). m.p.157-9℃. 1 H NMR (400MHz, CDCl 3 ): δ7.60-7.20(m, 11H), 6.60-6.62(m, 1H), 5.80(br, 1H), 5.71(s, 1H), 5.64(s, 1H), 5.05-4.90(m, 2H ), 4.69(d, J=3.2Hz, 1H), 4.66(s, 1H), 4.42(br, 1H), 4.35-4.25(m, 3H), 4.11(br, 2H), 4.05-3.98(m, 1H), 3.92-3.81(m, 2H), 3.80-3.65(m, 5H), 3.64-3.55(m, 2H), 3.46(s, 3H), 3.39(br, 1H), 3.27(s, 3H) , 2.55-2.42(m, 2H), 2.35-2.22(m, 2H), 2.10-1.98(m, 2H), 1.82-1.67(m, 4H). 13 C NMR (100MHz, CDCl 3 ):δ137.65,137.42,129.00,128.56,128.40,128.04,126.30,126.01,102.31,101.40,101.21,74.70,73.80,71.67,70.22,69.94,69.04,68.90,62.41,61.72,59.38,58.52,55.48, 55.09, 49.23, 47.41, 34.18, 31.68, 29.96, 27.96. IR (KBr): 3421, 2933, 2875, 1486, 1452, 1378, 1266, 1133, 1112, 1087, 972, 819, 754, 689. MS (ESI )m / z(%)...

Embodiment 3

[0028] Under the protection of nitrogen at 5Mpa, 2mmol of styrene was catalyzed by the product in Example 2 of 0.01mmol and stirred in 3mL of toluene at 60°C for 17 hours. GLC followed the reaction and found that the conversion of styrene was complete and the selectivity of aldehydes Nearly 100%, 95% of which is 2-methylphenylacetaldehyde.

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Abstract

The invention discloses a making method of chiral rhodium complex compound and application as catalyst, which is characterized by the following: adopting carbohydrate as starting material to make imidazoline salt with carbohydrate; generating rhodium complex compound coordinated by derivated N-heterocyclic carbene; displaying high catalytic property in the olefin hydroformylation reaction under 5Mpa in the nitrogen; improving transmitting rate in the GLC tracing course.

Description

technical field [0001] The present invention relates to the preparation of a class of chiral rhodium complexes and their application as catalysts, in particular to a method for preparing carbohydrate-coordinated rhodium complexes based on inexpensive carbohydrates and the use of rhodium complexes The application of the compound as a high-performance catalyst in the olefin hydroformyl reaction. technical background [0002] The 2-position hydrogen of imidazolinium salt is easy to be removed in the form of proton to form imidazolinyl-2-carbene. Some people call it the analogue of phosphine ligand, which is a very important kind of ligand. E. Bappert disclosed in SYLETT 2004, 1789-1793 the catalytic use of a class of rhodium complexes coordinated by chiral imidazolinium salts in asymmetric hydrogenation reactions. Carbohydrates have a wide range of sources and rich stereochemistry, but their derived chiral imidazolinium salts have not been reported so far. Contents of the in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00B01J31/12B01J31/28C07C45/50C07C45/67
Inventor 施继成童庆松贾莉雷霓
Owner FUJIAN NORMAL UNIV