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Sulfonylation/cyclization reaction method of 1, 6-eneyne and sulfonyl chloride driven by visible light

A visible light and sulfonylation technology, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as high reaction temperature, and achieve mild reaction conditions and a wide range of applications

Active Publication Date: 2020-06-30
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Nevertheless, these works are still plagued by at least one of the following limitations: (1) use of transition metal catalysts; (2) use of equivalent bases; (3) require higher reaction temperatures and organic chemicals as reaction media

Method used

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  • Sulfonylation/cyclization reaction method of 1, 6-eneyne and sulfonyl chloride driven by visible light
  • Sulfonylation/cyclization reaction method of 1, 6-eneyne and sulfonyl chloride driven by visible light
  • Sulfonylation/cyclization reaction method of 1, 6-eneyne and sulfonyl chloride driven by visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030]Add 1,6-enyne compound (39.8mg, 0.2mmol) shown in the Schlenk bottle in the formula 1a, the sulfonyl chloride compound (57.0mg, 0.3mmol) shown in the formula 2a and tetrahydrofuran (2mL), then react The device was stirred and reacted under an air atmosphere at 25°C under a 3W blue LED lamp, and the reaction process was monitored by TLC until the raw materials disappeared (reaction time was 36 hours). After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove the solvent, and the remaining The product was separated by column chromatography (elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1 (83% yield); 1 H NMR (500MHz, CDCl 3 )δ: 7.73(d, J=8.0Hz, 2H), 7.66(d, J=8.5Hz, 2H), 7.39(t, J=8.0Hz, 2H), 7.26-7.24(m, 2H), 7.20- 7.17(m, 1H), 5.43-5.41(m, 1H), 5.36-5.35(m, 1H), 4.69-4.66(m, 1H), 4.51-4.47(m, 1H), 3.87(d, J=14.5 Hz, 1H), 3.48(d, J=14.5Hz, 1H), 2.37(s, 3H), 1.38(s, 3H); 13 C NMR (125 ...

Embodiment 2

[0032] Ethyl acetate (2 mL) was used to replace tetrahydrofuran, and the remaining conditions were the same as in Example 1, and the yield of the target product I-1 was 13%.

Embodiment 3

[0034] Ethanol (2 mL) was used instead of tetrahydrofuran, and the other conditions were the same as in Example 1 to obtain the target product I-1 with a yield of 17%.

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Abstract

The invention relates to a visible-light-driven sulfonylation / cyclization reaction method of a 1, 6-enyne compound and a sulfonyl chloride compound in the absence of a photocatalyst and an additive system. The method comprises the following steps: adding the 1, 6-enyne compound, the sulfonyl chloride compound and a solvent into a Schlenk reaction bottle, and carrying out a stirring reaction undera 3W blue LED lamp at a certain temperature under an air atmosphere condition to obtain a sulfonylation / cyclization product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and specifically relates to a visible light-driven sulfonylation / cyclization reaction method of 1,6-enyne compounds and sulfonyl chloride compounds without a photocatalyst and additive system. Background technique [0002] Visible light-driven chemical reactions have aroused great interest in both academia and industry because of the characteristics of environmental friendliness, unlimited usability, and safety of visible light. Traditionally, such reactions usually require the help of external photocatalysts (transition metal complexes, organic dyes, or inorganic semiconductors) to absorb visible light and initiate subsequent chemical transformations, which are often indispensable. Recently, the emergence of photochemical reactions without photocatalyst systems has brought new ideas and possibilities for organic synthesis reactions under mild conditions. However, although great progress has b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07D207/38C07D401/12C07D409/12
CPCC07B61/02C07D207/38C07D401/12C07D409/12
Inventor 黄训杰魏文廷曹婷婷孟潇潇宋思哲
Owner NINGBO UNIV
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