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A kind of method and application of synthesizing organosulfur compound based on alkyl xanthate

A technology of alkyl xanthate and organic sulfur, which is applied in the direction of organic chemistry, organic chemistry, chemical instruments and methods, etc., can solve the problem of harsh reaction conditions for the synthesis of sulfur compounds, poor compatibility of functional groups, and low total yield of reactions, etc. problems, to achieve the effect of easy access, low cost and high selectivity

Active Publication Date: 2022-07-29
NANJING NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0005] Aiming at the problems existing in the prior art, the present invention provides a method for synthesizing organosulfur compounds based on alkyl xanthate and its application, which solves the harsh synthesis reaction conditions of existing sulfur compounds, the toxicity or pungent smell of vulcanizing reagents 1. The use of noble metal catalysts is resistant to strong alkalis, the total yield of the reaction is low, the compatibility of functional groups is poor, the scope of application is narrow, and the environmental protection, safety, and economy of reagents are prominent problems.

Method used

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  • A kind of method and application of synthesizing organosulfur compound based on alkyl xanthate
  • A kind of method and application of synthesizing organosulfur compound based on alkyl xanthate
  • A kind of method and application of synthesizing organosulfur compound based on alkyl xanthate

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Experimental program
Comparison scheme
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Embodiment 1

[0031]

[0032] Under nitrogen protection, nickel chloride ethylene glycol dimethyl ether complex (0.05 mmol), 6,6'-dimethyl-2,2'-bipyridine (0.05 mmol) were sequentially added to a 25 mL reaction flask, Alkyl xanthate 1a (0.5 mmol), electrophile 2a (0.6 mmol), N,N-dimethylpropenylurea (2.5 mL), potassium iodide (0.25 mmol) and elemental zinc (1.5 mmol). After mixing uniformly at room temperature, the reaction mixture was reacted at 40 °C for 12 h. After the reaction was completed, 5 mL of water was added, extracted with ethyl acetate (5 mL×3), the organic phases were combined, the solvent was evaporated under reduced pressure, and then separated by column chromatography (petroleum ether:ethyl acetate V / V=10:2) to obtain Compound 1, IR (neat): 2360, 1780, 1714, 1468, 1207, 901, 773, 716, 684, 646. 1 HNMR (400 MHz, CDCl 3 ): δ 7.98 – 7.91 (m, 2H), 7.91 – 7.84 (m, 2H), 7.80 – 7.73(m, 2H), 7.65 – 7.55 (m, 1H), 7.52 – 7.41 (m, 2H), 6.40 – 6.30 (m , 1H), 2.82 – 2.67 (m, 1H)...

Embodiment 2

[0034]

[0035] Under nitrogen protection, nickel bromide ethylene glycol dimethyl ether complex (0.05 mmol), 1,10-phenanthroline (0.05 mmol), and alkyl xanthate 1a (0.5 mmol) were sequentially added to a 25 mL reaction flask. mmol), electrophile 2b (0.7 mmol), N,N-diacetamide (2.5 mL), (Boc) 2 O (1.4 mmol), magnesium chloride (0.7 mmol) and elemental zinc (1.5 mmol). After mixing uniformly at room temperature, the reaction mixture was reacted at 40 °C for 10 h. After the reaction was completed, 5 mL of water was added, extracted with ethyl acetate (5 mL×3), the organic phases were combined, the solvent was evaporated under reduced pressure, and then separated by column chromatography (petroleum ether:ethyl acetate V / V=10:2) to obtain Compound 2, IR (neat): 2920, 2360, 2342, 1760, 1377, 1084, 882, 750, 717, 528. 1 HNMR (400 MHz, CDCl 3 ): δ 7.87 (m, 2H), 7.79 – 7.70 (m, 2H), 7.27 (m, 1H), 7.24(s, 1H), 7.16 (m, 3H), 6.10 (m, 1H), 2.69 – 2.54 (m, 5H), 2.54 – 2.35 (m, 3H...

Embodiment 3

[0037]

[0038] Under nitrogen protection, nickel chloride ethylene glycol dimethyl ether complex (0.05 mmol), 6,6'-dimethyl-2,2'-bipyridine (0.05 mmol) were sequentially added to a 25 mL reaction flask, Alkyl xanthate 1a (0.5 mmol), Electrophile 2c (0.7 mmol), N,N-Dimethylpropenylurea (2.5 mL), (Boc) 2 O (1.4 mmol), magnesium chloride (0.7 mmol) and elemental zinc (1.5 mmol). After mixing uniformly at room temperature, the reaction mixture was reacted at 40 °C for 12 h. After the reaction was completed, 5 mL of water was added, and extracted with ethyl acetate (5 mL×3), the organic phases were combined, the solvent was evaporated under reduced pressure, and then separated by column chromatography (petroleum ether:ethyl acetate V / V=10:2) to obtain the compound 3. IR (neat): 3853, 3675, 2987, 2360, 2342, 1717, 1559, 1395, 1066, 669. 1 H NMR (400 MHz, CDCl 3 ): δ 10.11 (s, 1H), 8.08 (d, J = 8.2 Hz, 2H), 7.96 (d, J = 8.3 Hz, 2H), 7.93 – 7.86 (m, 2H), 7.83 – 7.73 (m, 2H...

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Abstract

The invention discloses a method for synthesizing organic sulfur compounds based on alkyl xanthate and its application. The method includes the following steps: in a solvent, using alkyl xanthate as a sulfur source, elemental zinc as a reducing agent, nickel as a catalyst, bipyridine and its derivatives as ligands, and coupling with an electrophile to synthesize organic compounds Sulfur compounds. The method of the invention has many advantages, such as stable sulfur source, low price and no irritating odor; wide and cheap sources of catalyst and ligand; simple and cheap reducing agent; mild reaction conditions and high selectivity; The substrate has a wide range of applications, and natural products and drug molecules are also compatible. Under the optimized reaction conditions, the yield of the target product is as high as 80% after separation.

Description

technical field [0001] The invention belongs to the field of catalytic synthesis technology and homogeneous metal-catalyzed coupling synthesis, and more particularly relates to a method for synthesizing organic sulfur compounds based on alkyl xanthates and applications thereof. Background technique [0002] Sulfur-containing chemical structures are widely distributed in natural products, pharmaceuticals, pesticides and advanced materials. It is worth noting that more than 25% of the top 200 drugs approved by the US FDA are sulfur-containing drugs. Due to its importance, efforts have been devoted to developing efficient methods for the construction of C–S bonds from various sulfur sources using transition metal catalysis. Among them, the most classical method for C–S bond formation relies on the use of organosulfur reagents such as thiols or disulfides as coupling agents under strong base conditions. However, the sulfur reagents used in such reports often have unpleasant od...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48C07D409/12C07D417/12C07C327/32C07C327/26C07C327/28C07C319/14C07C321/20C07D317/24C07F7/10C07B45/06C07B45/00
CPCC07D209/48C07D409/12C07D417/12C07C327/32C07C327/26C07C327/28C07C319/14C07F7/083C07D317/24C07B45/06C07B45/00C07C2601/08C07C321/20
Inventor 陈良安陈莉台蓝珠
Owner NANJING NORMAL UNIVERSITY
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