Organozinc reagent is one of the earliest organometallic reagents discovered. Due to the low reactivity of the organozinc reagent, it has the advantages of good functionality, high solid compatibility, chemical region and stereoselectivity.
In addition, organic zinc reagents can undergo metal exchange reactions with many transition metal salts or complexes to obtain highly active organic transition metal reagents, which can react with a variety of electrophilic reagents.
This paper mainly studies the application of organozinc reagents in elongation and C-C bond [1, 2] migration reactions. In addition, the ring-opening reaction of 1,2-disubstituted cyclopropanol under various conditions was also studied.
This paper is divided into five chapters.
Chapter 1: Preparation of organozinc reagents and their application in organic synthesis
Firstly, a detailed review is given on the development of machine tests and key components, and then on the preparation of halogenated organozinc reagents and their application in organic synthesis.
Chapter 2: The application of organozinc reagents in the ring expansion and carbon chain elongation reactions of -eryu
This chapter The ring expansion and carbon chain elongation reaction of p-dione promoted by the organozinc reagent FCO2C was studied, and r-dione with extended carbon chain was obtained in a moderate to high yield. Under the condition of excess mixed organozinc reagent, β-diketone can undergo carbon chain extension/cyclopropanation reaction, and trans-1,2-disubstituted cyclopropanol can be obtained with high yield and stereospecificity. At the same time, we also studied the electronic effects and steric hindrance effects of substituent groups on the reaction yield and regioselectivity.
Chapter 3: Research The application of organic reagents in the ALdol condensation of α-bromoketone and the C-C bond [1, 2] migration reaction
This chapter developed a method based on a -A new method for preparing β-diketones using bromoketone as raw material and using Furukawa reagent EtZnCH2I. Under mild experimentation, aromatic α-bromomethyl ketones can be converted into β-diketones in a new way. The reaction proceeds via a Reformatsky-type reaction of a-bromoketone and C-C bond migration. For lipid-resistant α-bromoketones, 2,4-disubstituted cyclopropanol and 1,2-disubstituted cyclopropanol were obtained in moderate yields depending on the reaction substrate, and their stereochemistry is cis- Configuration, based on the experimental results, we proposed a possible mechanism for this reaction.
Chapter 4: Reported on the application of Et2Zn in the rearrangement reaction of β-bromoalcohol Semipinacol
This chapter studies in detail the reaction of Et2Zn-promoted rearrangement of -bromoalcohol Semipinacol to produce carbonyl compounds. It has the following advantages: mild reaction conditions, high conversion rate, functional compatibility and lower than stoichiometry. Reaction reagents, etc.
Chapter 5: Study on the ring-opening reaction of 1,2 disubstituted cyclopropanol under the action of copper salt, acid and base
This chapter studies in detail the ring-opening reaction of 1,2 disubstituted cyclopropanol prepared from β-bis under the action of copper nitrate, p-toluenesulfonic acid and sodium hydroxide. .
