Method for cross coupling of N-arylamine and cyclic ketoxime ester C (sp3)-C (sp3) through photooxidation reduction catalysis

Abstract

The invention discloses a method for cross coupling of N-arylamine and cyclic ketoxime ester C (sp3)-C (sp3) through photooxidation reduction catalysis. According to the method, cyclic ketoxime ester is taken as a cyanogen alkylation reagent, C (sp3)-C (sp3) cross-coupling reaction of N-arylamine and cyclic ketoxime ester is realized under the condition of no metal catalysis, various N-arylamine and cyclic ketoxime ester are converted into corresponding target compounds at good to excellent yield under mild conditions, and the method has a wide reaction substrate application range. The synthesis strategy can be applied to structural modification of d-aminocarbonyl compounds and oligopeptide compounds. According to the present invention, the catalytic reaction condition is mild and simple, the catalytic reaction can be smoothly performed at the room temperature by using the 3CzClIPN as the catalyst, the reaction controllability is high, the cost is low, the high regioselectivity can be obtained without using the metal catalyst, the alkali and/or the other ligand, and the method is suitable for the large-scale production;

Description

technical field [0001] This application belongs to the technical field of organic synthesis methodology, and specifically relates to a photoredox catalyzed N-arylamine and cyclic ketoxime ester C(sp 3 )-C(sp 3 ) cross-coupling method. Background technique [0002] Functional amine compounds are considered to be important structural units and widely exist in the structures of drug molecules and natural products. Due to their rich chemical and biological activities, the development of general synthetic strategies to prepare and / or modify this class of compounds has attracted increasing attention. Among the reported methods, the alkylation of N-arylamines is one of the most efficient ways to produce nitrogen-containing organic compounds, which introduces C(sp 3 ) part to change the spatial conformation and increase the lipophilicity and hydrophilicity of the drug compound. Typical methods for the alkylation of N-arylamines mainly rely on CDC (cross-dehydrocoupling) reaction...

AI Technical Summary

Problems solved by technology

Typical methods for the alkylation of N-arylamines mainly rely on CDC (cross-dehydrocoupling) reactions, and although significant progress has been made in this area, there are still considerable limitations: (1) Most methods rely heavily on In activated alkyl C(sp 3 )-H bonds adjacent to heteroatoms (such as O, S, and N) or electron-withdrawing groups (such as nitriles, esters, ketones, and amides)

(2) usually require superstoichiometric oxidants and high temperatures, resulting in poor chemoselectivity and atom economy

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