1,2,3‑triazole monosubstituted 1,3,5‑s-triazine compounds synergistically cuso 4 ·5h 2 o Catalytic decarboxylation coupling reaction method

Abstract

The invention discloses a method for catalyzing decarboxylation coupling reaction by a 1,2,3-triazole monosubstituted 1,3,5-s-triazine compound coordinated with CuSO4.5H2O. By taking CuSO4.5H2O which is good in stability and cheap and easily available and the triazine compound which is stable in water and air and high in functionalization as a catalytic system, the method catalyzes decarboxylation coupling reaction on aryl halide and phenylpropiolic acid. The reaction system is free of a conventional phosphine ligand, so that the environmental pollution is reduced, and the method has good substrate applicability. The target product is easy to separate and purify and high in yield. The method disclosed by the invention is an efficient and safe decarboxylation coupling reaction system and can be applied to constructing Csp-CsP2 bonds.

Description

technical field [0001] The invention belongs to the technical field of decarboxylation coupling reaction, and specifically relates to a 1,2,3-triazole monosubstituted 1,3,5-s-triazine compound synergized with CuSO 4 ·5H 2 O catalyzed decarboxylation coupling reaction method. Background technique [0002] Alkynes are an important class of species for efficient construction of organic synthesis units. At present, transition metal-catalyzed coupling reactions are the main method for synthesizing alkynes, and common reactions include classic organic reactions such as Negishi, Stille, and Sonogashira. However, these reactions usually have many disadvantages: 1. Metal reagents need to be prepared in advance; 2. These metal reagents are sensitive to water and air; 3. Metal reagents require multifunctional compatibility; 4. Acetylene gas is difficult to handle as an alkyne source; Methylsilylacetylene will produce an equivalent amount of organic waste after the reaction; 6. The i...

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Problems solved by technology

However, these reactions usually have many disadvantages: 1. Metal reagents need to be prepared in advance; 2. These metal reagents are sensitive to water and air; 3. Metal reagents require multifunctional compatibility; 4. Acetylene gas is difficult to handle as an alkyne source; Methylsilylacetylene will produce an equivalent amount of organic waste after the reaction; 6. The introduced bis(tributyltin)acetylene needs a strong base to deprotect

However, it cannot be ignored that the existence of various Cu catalytic systems requires harsher reaction conditions and lower catalytic efficiency. For example, more active and unstable copper salts and electron-rich ligands are needed to improve Cu Efficiency and activity of the catalyzed deacidification coupling reaction

However, such ligands are usually not friendly to the environment, and are used in large amounts in some systems, which can easily cause environmental pollution.