Preparation method of olefin and method for synthesizing Chondriamide A and Chondriamide C

Abstract

The invention provides a preparation method of olefin and a method for synthesizing Chondriamide A and Chondriamide C. The preparation method of olefin comprises the steps as follows: a compound withthe structure shown in a formula (I), a palladium catalyst, a phosphorus ligand, alkali and an organic solvent are mixed and react at the normal temperature under light, and olefin with the structureshown in a formula (II) is obtained. Through selection of the specific phosphorus ligand, the method can realize efficient catalytic conversion at the room temperature under the action of photocatalysis, has mild reaction conditions, is simple to operate, meets the requirement for developing green and environment-friendly chemistry, and has more universal substrate selection range and functional group compatibility and excellent chemical selectivity. The method can be successfully applied to a scheme for introducing C-C double bonds in complex molecules and a synthesis strategy for optimizingpart of drug molecules, can improve the synthesis efficiency and reduce the cost and has industrial synthesis value and prospects.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing olefins and synthesizing Chondriamide A and Chondriamide C by decarboxylation of aliphatic carboxylic acids. Background technique [0002] Alkenes are a very important class of synthetic intermediates in organic chemistry. Various other groups can be easily introduced through the reaction of alkenes, such as the preparation of halogenated compounds through addition reactions, and the preparation of cyclic compounds through D-A reactions; on the other hand, alkenes are also Various coupling reactions can occur through Heck reaction, Suzuki reaction, etc. It is widely used in the field of synthesis. [0003] At present, reports on the reaction of aliphatic carboxylic acid decarboxylation to olefins are quite extensive, such as palladium catalysis (Angew.Chem.Int.Ed.2015, 54, 11800-11803), copper catalysis (Angew.Chem.Int.Ed.2017, 56, 7648-7652), etc., but s...

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Problems solved by technology

[0003] At present, reports on the reaction of aliphatic carboxylic acid decarboxylation to olefins are quite extensive, such as palladium catalysis (Angew.Chem.Int.Ed.2015, 54, 11800-11803), copper catalysis (Angew.Chem.Int.Ed.2017, 56, 7648-7652), etc., but some of the currently disclosed reactions to prepare olefins from aliphatic carboxylic acid decarboxylation require higher reaction temperatures (130° C.), or use equivalent heavy metal catalysts (equivalent lead acetate), which are harmful to the environment. It caused relatively large pollution; therefore, it is of great significance to prepare corresponding olefins through low-pollution means using carboxylic acids widely existing in nature, which is in line with the requirements of green chemistry.

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