Method for preparing 2-iodo-1-phosphoryl substituted alkane compound through efficient olefin bifunctionalization

Abstract

The invention provides a method for efficiently and highly selectively synthesizing a substituted 2-iodo-1-phosphoryl substituted alkane compound containing different functional groups. N-iodosuccinimide (NIS) is used as an accelerant, a compound containing P(O)-OH and olefin are used as reaction substrates, and an organic solvent is added into a reaction system. The method has the advantages thatthe accelerant is cheap and easy to obtain; the substrate applicability is high; reaction conditions are mild, safe and reliable; the selectivity of the obtained target product is close to 100%; andthe yield is as high as 90% or above. According to the method, a new way for synthesizing the substituted 2-iodo-1-phosphoryl substituted alkane compound containing different functional groups is developed, the defects of poor reaction selectivity, complex reaction steps, low yield, need of reagents harmful to the environment and the like in traditional synthesis of the 2-iodo-1-phosphoryl substituted alkane compound are overcome, and the method has a good industrial application prospect. The invention also provides a corresponding substituted 2-iodo-1-phosphoryl substituted alkane derivativecontaining different functional groups.

Description

technical field [0001] The invention relates to the field of catalytic synthesis of organophosphate compounds, in particular to a method for preparing 2-iodo-1-phosphoryl substituted alkane compounds through efficient difunctional reaction of P(O)-OH compounds and olefins. Background technique [0002] Organophosphate compounds are an important class of organic compounds in organic synthesis. This type of compound has good catalytic activity, optical activity and biological activity, making it useful in biology, medicine, optically active materials and asymmetric catalytic synthesis. Wide range of applications. As we all know, phosphorus and organophosphorus compounds are important substrates in life, such as ADP, ATP, RNA and organophospholipid bilayers in the human body. However, it is difficult to find pure natural organic phosphate compounds in nature, and most of the phosphorus elements exist in nature in the form of inorganic salts. Most of the known organic phosphate...

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Problems solved by technology

However, the above-mentioned methods generally use air-sensitive reagents (P(O)-H compounds, carbon tetrachloride, sulfuryl chloride, etc.), and there are also problems such as cumbersome experimental steps, expensive catalysts and difficult recycling, harsh reaction conditions, Defects such as cross-substrate applicability, low yield, and large environmental pollution

[0004] So far, the high-efficiency synthesis of 2-iodo-1-phosphoryl substituted alkane compounds still has the quality of raw materials and the safety of production (compounds such as phosphorus trichloride, phosphorus pentachloride and phosphorus oxychloride are relatively corrosive) and There are several problems such as product stability and purity, and the synthesis technology is relatively difficult. At present, only a few companies in the United States, Japan and other countries are producing, and the current situation of my country's high-end organic phosphate products mainly relies on imports.

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