Synthetic Methods for Heterocycles and Carbocycles Bearing Fluorinated One-Carbon Units (=CF<sub>2</sub>, CHF<sub>2</sub>, or CF<sub>3</sub>): Intramolecular Reaction of 2-Trifluoromethyl-1-alkenes

DOI Web Site 21 Citations 283 References
  • Ichikawa Junji
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba

Bibliographic Information

Other Title
  • Synthetic methods for heterocycles and carbocycles bearing fluorinated one-carbon units (= CF2, CHF2, or CF3): intramolecular reaction of 2-trifluoromethyl-1-alkenes

Search this article

Abstract

Fluorine-containing heterocyclic and carbocyclic compounds attract widespread attention as important components of agrochemicals, pharmaceuticals, materials, and catalysts. To provide a general route to these compounds, we have developed a new methodology to construct fluorocarbon-bearing cyclic systems based on ring closure of functionalized 2-trifluoromethyl-1-alkenes, readily obtained from commercially available CH2=C(CF3)Br or CF3CO2Et. Their intramolecular reactions, such as nucleophilic substitution or addition, alkene insertion, and electrocyclization, provide a wide variety of five- and six-membered heterocycles and carbocycles bearing a fluorinated one-carbon unit (a =CF2, CHF2, or CF3 group). To construct five-membered rings, we successfully accomplished a nucleophilic 5-endo-trig cyclization and 5-endo alkene insertion, normally disfavored processes, as well as fluorine-directed Nazarov cyclization.

Journal

Citations (21)*help

See more

References(283)*help

See more

Keywords

Details

Report a problem

Back to top