Trifluoromethoxylation/trifluoromethylthiolation/trifluoro- methylselenolation strategy for the construction of heterocycles

The XCF3 groups (X = O, S, Se) play an increasingly important role in modern organic chemistry due to their unique electronegativity, lipophilic nature, metabolic stability, and bioavailability. Heterocyclic compounds are important scaffolds in many bioactive compounds and drugs. The incorporation o...

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Veröffentlicht in:Chinese chemical letters 2023-05, Vol.34 (5), p.108045, Article 108045
Hauptverfasser: Wang, Xin, Wang, Zhichuan, Li, Zhenjian, Sun, Kai
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Sprache:eng
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Zusammenfassung:The XCF3 groups (X = O, S, Se) play an increasingly important role in modern organic chemistry due to their unique electronegativity, lipophilic nature, metabolic stability, and bioavailability. Heterocyclic compounds are important scaffolds in many bioactive compounds and drugs. The incorporation of XCF3 groups into heterocyclic compounds can change their physicochemical and biological properties, which injects new vitality into the application of heterocyclic compounds in many fields such as organic chemistry, the pharmaceutical chemistry, and life sciences. In this paper, the recent progress in the synthesis of F3CX-containing heterocycles is reviewed, and the application scope and mechanism of some reactions are discussed. In this review, the synthesis of trifluoromethoxylated, trifluoromethylthiolated, and trifluoromethylselenolated heterocyclic compounds, classified as (i) direct CH trifluoromethoxylation/trifluoromethylthiolation/trifluoromethylselenolation of heterocycles; (ii) cyclization of alkenes/alkynes to synthesize F3CO (S, Se)-containing heterocycles, as well as other types, is described. [Display omitted]
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2022.108045