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A method for preparing α-alkynyl γ-cyano functionalized ketones from allyl alcohol

A technology of cyano function and allyl alcohol, which is applied in the field of difunctionalization reaction of free radical process, can solve the problems of product metal residue, transition metal and ligand expensive, etc., achieve mild reaction conditions and a wide range of substrates , The effect of a simple source of cyanide

Active Publication Date: 2022-05-31
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the past, the synthesis of γ-cyanoketones usually involved catalytic equivalents of transition metals, various complex ligands and excess oxidants (Org.Lett . 2012,14,9,2414; ACS Catal.2018,8,11324; Angew.Chem.Int.Ed.2016,55,2866.), transition metals and ligands are expensive in the above method, and the metal residues in the product and other unavoidable disadvantages

Method used

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  • A method for preparing α-alkynyl γ-cyano functionalized ketones from allyl alcohol
  • A method for preparing α-alkynyl γ-cyano functionalized ketones from allyl alcohol
  • A method for preparing α-alkynyl γ-cyano functionalized ketones from allyl alcohol

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Embodiment 1

[0031] [4-benzoyl-4-methyl-6-phenylhex-5-ynenitrile]

[0032]

Embodiment 2

[0036] [4-benzoyl-4-methyl-6-(4-propylphenyl)hex-5-ynenitrile]

[0037]

Embodiment 3

[0041] [4-benzoyl-4-methyl-6-(4-propylphenyl)hex-5-ynenitrile]

[0042]

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Abstract

The invention belongs to the technical field of difunctionalization reactions of free radical processes, and specifically relates to a method for preparing α-alkynyl γ-cyano functionalized ketones from allyl alcohols. Difunctionalization of Alcohols with Alkyl Nitriles to Prepare a Series of α-Alkynyl γ-Cyano-functionalized Ketones. The specific process steps are: in the dehydrated and deoxygenated Schlenk tube (Schlenk tube), add raw material allyl alcohol, initiator, and nitrile solvent in proportion, place the above-mentioned Schlenk tube in an oil bath at 120°C, and stir for 12 Hour. Finally, through silica gel column chromatography, the α-alkynyl γ-cyano functionalized ketone product is obtained. The present invention involves the formation of alkylnitrile radicals, their subsequent intermolecular addition to alkenes and migration of 1,2-alkynyl groups to give a series of α-alkynyl γ-cyano functionalized ketones.

Description

A kind of method for preparing α-alkynyl γ-cyano functionalized ketone from allyl alcohol technical field The invention belongs to the bifunctionalization reaction technical field of free radical mechanism, what be specifically related to is α-aryl α-alkynyl Difunctionalization of allyl alcohols, particularly involving the use of organic peroxides to promote the difunctionalization of nitriles with α-aryl α-alkynyl allyl alcohols The functional grouping reaction gave α-alkynyl-γ-cyano functional ketones in moderate and excellent yields. Background technique [0002] Radical-mediated difunctionalization of olefins is a hot topic in organic chemistry. Among them, by molecular The bifunctionalization of unactivated alkenes by internal functional group migration has attracted the attention of many researchers. Among them, Academician Tu Yongqiang Published in Chemical Society Reviews an article titled "Radical aryl migration reactions and synthetic applications”, and d...

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/40C07D307/54C07D333/24C07B41/06
CPCC07C253/30C07D307/54C07D333/24C07C255/40C07B41/06Y02P20/584
Inventor 孙松金盛楠成江周聪
Owner CHANGZHOU UNIV