Chinese Journal of Organic Chemistry >
Advances in Trifluoromethylation-Promoted Functional Group Migration of Alkenes
Received date: 2020-09-15
Revised date: 2020-11-18
Online published: 2020-12-05
Supported by
Special Funds for Fundamental Scientific Research of Central Universities(LGZD202006); College Students' Practice and Innovation Training Program(201912213019G); College Students' Practice and Innovation Training Program(201912213023G)
The incorporation of trifluoromethyl functional groups can effectively improve the chemical stability, metabolic stability and liposolubility of functional molecules. Therefore, the development of efficient methods to synthesize trifluoromethyl compounds is of significant importance. In recent years, great progress has been made in the reaction of a trifluoromethyl radical and alkene, in which alkyl radical species was first formed, followed to promote intramolecular functional groups migration. The novel pathways not only provide practical strategy for the functionalization of alkenes, which can realize the rapid construction of diverse molecules, but also promote the development of organic radical chemistry. The recent advances in alkene trifluoromethylation-initiated functional group migration including functionalized allylic compounds and non-activated alkenes are sumarrized. According to different types of migrating functional groups, the reaction in the two different sections are classified, in which the pathways of free radical generation, the scope and limits of the reaction and the reaction mechanism in different catalytic systems are discussed and highlighted in detail. Finally, a perspective on the further development of this research area is made.
Key words： alkene; trifluoromethylation; migration; difunctionalization; radical
Yunliang Qiu , Fengjiao Wei , Liu Ye , Minyue Zhao . Advances in Trifluoromethylation-Promoted Functional Group Migration of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 1821 -1834 . DOI: 10.6023/cjoc202009036
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