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Alkylation/acylation method of photooxidation reduction/copper co-catalysis

A photo-oxidation and co-catalysis technology, applied in the direction of organic chemistry, etc., can solve the problems of limited use of strong bases and narrow waste, and achieve mild and simple reaction conditions, excellent yield and good adaptability.

Active Publication Date: 2021-04-20
NANCHANG HANGKONG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although great achievements have been made, this available method is still limited by the use of strong bases, the narrow reaction substrate range and the large amount of waste generated by the process

Method used

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  • Alkylation/acylation method of photooxidation reduction/copper co-catalysis
  • Alkylation/acylation method of photooxidation reduction/copper co-catalysis
  • Alkylation/acylation method of photooxidation reduction/copper co-catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] In the Schlenk lock reactor, add the indazole (0.2mmol) of 1a, the bicyclobutanoyl peroxide (2equiv, 0.4mmol) shown in formula 2m, CuBr (20mol%, 0.04mmol), [Ir(dtbbpy )(ppy) 2 ]PF 6 (1mol%, 0.002mmol), 1,10-Phen ( 30mol%, 0.06mmol) and 1,4-dioxane (2mL), the atmosphere in the reactor was replaced with argon, then the reactor was placed under the irradiation of a 18W blue LED lamp, and the reaction was stirred at 100°C until The complete consumption of raw materials was monitored by TLC and / or GC-MS. After the reaction was complete (24 h), the residue was concentrated under reduced pressure to obtain a residue, which was separated by silica gel column chromatography (petroleum ether / ethyl acetate) to obtain the target product. Yellow oily liquid (25.8mg, 75% yield, R f =0.9(PE / EA=20:1)); 1 H NMR (500MHz, CDCl 3 )δ8.02(s,1H),7.71(d,J=8.5Hz,1H),7.43(d,J=8.5Hz,1H),7.34(m,1H),7.15-7.09(m,1H), 5.10-5.03(m,1H),2.85-2.77(m,2H),2.52-2.47(m,2H),2.01-1.88(m,2H);...

Embodiment 2

[0041] Replace photocatalyst with Ir(ppy) 3 , other conditions are the same as in Example 1, and the reaction cannot be carried out.

Embodiment 3

[0043] Replace photocatalyst with Ru(bpy) 3 Cl 2 ·6H 2 O, other conditions are the same as Example 1, and the reaction cannot be carried out.

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Abstract

The invention discloses an alkylation / acylation method of photooxidation reduction / copper co-catalysis. According to the invention, the method comprises the steps: taking novel diacyl peroxide as an alkylation / acylation reagent, and introducing different alkyl (secondary alkyl) or acyl (tertiary alkyl) into various different nitrogen-containing nucleophilic reagents under the common catalysis condition of copper catalysis and photooxidation reduction catalysts, wherein the reaction conditions are mild and simple, economy and cheapness are achieved, the yield is excellent, and the reaction substrate adaptability is good.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, in particular to a free radical-mediated decarboxylation C(sp 3 )-N cross-coupling reaction method. Background technique [0002] In the past few decades, due to the important role of C-N bonds in drugs, natural products and pesticides, the construction of C-N bonds has been a focus area of ​​organic synthesis, where C(sp 3 )-N bond formation has attracted extensive attention. Therefore, many form C(sp 3 )-N bond strategies include coupling nitrogen nucleophiles with alkyl electrophiles (e.g., aliphatic halides, alcohols, etc.), reductive amination, hydroamination of alkenes, and carboamination of alkenes. Although great achievements have been made, this available method is still limited by the use of strong bases, the narrow reaction substrate range and the large amount of waste generated by the process. [0003] Aliphatic carboxylic acids and their derivatives are inexpensive, s...

Claims

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Application Information

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IPC IPC(8): C07D231/56C07D401/04
Inventor 欧阳旋慧温著东宋仁杰李金恒唐梓亮
Owner NANCHANG HANGKONG UNIVERSITY
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