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Method for selectively generating trans-macrocycloalkene by gold-catalyzed intramolecular diazo coupling

A selective, macrocyclic alkene technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of lack of selectivity of double bond cis-trans isomerism, and achieve high stereoselectivity and operation. Simple, high-yield effects

Active Publication Date: 2015-11-11
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] (1) Rh-catalyzed diazonium coupling generates cyclic olefins. The disadvantage of this method is that the cis-trans isomerization of the double bond is not selective

Method used

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  • Method for selectively generating trans-macrocycloalkene by gold-catalyzed intramolecular diazo coupling
  • Method for selectively generating trans-macrocycloalkene by gold-catalyzed intramolecular diazo coupling
  • Method for selectively generating trans-macrocycloalkene by gold-catalyzed intramolecular diazo coupling

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Experimental program
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Effect test

Embodiment 1

[0022]

[0023] Synthesis of 2a: add to a dry reaction vial under argon atmosphere t BuXphosAuCl (35mg), NaBAr F (44mg), 1a (772mg), 1,2-dichloroethane (20mL), the reaction was heated up to 80 degrees Celsius and stirred for 12 hours; the reaction solution was cooled, the solvent was evaporated under reduced pressure, and column chromatography gave compound 2a (462mg, Yield:70%) is a white solid, mp:83-85°C; 1 HNMR (400MHz, CDCl 3 )δ6.99(s,2H),6.93-6.75(m,4H),3.96(t,J=5.5Hz,4H),2.67-2.64(t,J=12.0Hz,4H),1.88-1.70(m ,8H),1.51(m,4H). 13 CNMR (100MHz, CDCl 3 )δ202.21, 148.54, 136.57, 120.66, 112.36, 67.94, 41.48, 29.57, 26.33, 26.13.

Embodiment 2

[0025]

[0026] Synthesis of 2b: add to dry reaction vial under argon atmosphere t BuXphosAuCl (35mg), NaBAr F (44mg), 1b (500mg), 1,2-dichloroethane (20mL), the reaction was heated up to 80 degrees Celsius and stirred for 12 hours; the reaction solution was cooled, the solvent was evaporated under reduced pressure, and column chromatography gave compound 2b (252mg, Yield: 65%); 1 HNMR (400MHz, CDCl 3 )δ7.03(s,2H),2.71-2.59(m,4H),1.89-1.71(m,4H),1.46(m,4H),1.28(m,4H). 13 CNMR (100MHz, CDCl 3 )δ203.18, 137.22, 39.12, 24.75, 24.51, 24.18.

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Abstract

The invention discloses a method for selectively generating trans-macrocycloalkene by gold-catalyzed intramolecular diazo coupling and belongs to the field of organic synthesis. The method comprises the following steps: adding a catalyst, NaBArF, 1,2-dichloroethane and a diazo compound into a dry reaction flask in an argon atmosphere; raising the temperature to 80 DEG C; and carrying out a reaction for 12 hours to obtain the trans-macrocycloalkene with high yield and high selectivity. The method has the advantages of being simple to operate, high in yield and good in stereoselectivity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a method for selectively generating trans macrocyclic olefins through gold-catalyzed intramolecular diazo coupling. Background technique [0002] Diazo compounds are important synthons in the field of organic synthesis, and the coupling of diazo compounds is an effective method for the preparation of macrocyclic alkenes. The methods of intramolecular diazo coupling reported in previous literature are: [0003] (1) Rh-catalyzed diazonium coupling to generate cyclic olefins, the disadvantage of this method is that the cis-trans isomerization of the double bond is not selective. [0004] [0005] Doyle, M.P.; Hu, W.; Phillips, I.M. Org. Lett. 2000, 2, 1777. [0006] (2) Ru-catalyzed diazonium coupling to generate cis-cyclic olefins, which is to selectively generate cis-olefins through Ru catalysis. [0007] [0008] Li, G.; Che, C. Org. Lett. 2004, 6, 1621. Con...

Claims

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Application Information

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IPC IPC(8): C07D321/00C07C45/65C07C49/413
CPCC07C45/65C07C49/413C07D321/00
Inventor 孙江涛
Owner CHANGZHOU UNIV
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