Application of BF3·Et2O in the synthesis of cyclic organic peroxides (microreview)

Abstract

A summary of recent applications of Lewis acid BF 3 ·Et 2 O as a catalyst in the synthesis of cyclic organic peroxides is presented.

Marriage of Peroxides and Nitrogen Heterocycles: Selective Three-Component Assembly, Peroxide-Preserving Rearrangement, and Stereoelectronic Source of Unusual Stability of Bridged Azaozonides

“…The dramatic expansion of medicinal chemistry of organic peroxides was inspired by >100 known peroxide-containing natural products. − The variety of natural examples lessened concerns associated with the perceived peroxide instability and led to research efforts aimed at the development of synthetic approaches to varied classes of cyclic peroxides including 1,2-dioxolanes, − 1,2,4-trioxolanes (ozonides), ,− 1,2-dioxanes, − 1,2,4-trioxanes, − 1,2,4,5-tetraoxanes, − cyclic triperoxides, and tricyclic mono- and bisperoxides. − …”

Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities

“…As a result, synthetic approaches have been developed for the synthesis of various classes of cyclic peroxides such as 1,2-dioxanes, − 1,2-dioxolanes, − 1,2,4-trioxanes, − 1,2,4-trioxolanes (ozonides), − bisperoxides, − and triperoxides. , Such peroxides display antiparasitic, ,− anticancer, ,− antifungal, ,, antitubercular, − and antiviral − activities. Synthetic peroxide OZ277 (“arterolane”) is used for the treatment of malaria.…”

Dual Catalysis Involving Organoboron Compounds

“…For example, BF 3 • Et 2 O is one of the most commonly used Lewis acid in synthetic chemistry. [4] In 1963, B(C 6 F 5 ) 3 (BCF) was first synthesized by Stone, Massey and Park, which was found to be a strong Lewis acid due to the strong electron-withdrawing effects of the three aryl rings with fifteen fluorine atoms. However, in the following decades, B(C 6 F 5 ) 3 did not attract much attention in the synthetic world except being used in Ziegler-Natta olefin polymerization as an activator.…”

“…Due to the ubiquitous electronic structure of elemental boron, which possess a strong electrophilic nature, boron catalysts often serve as Lewis acids. For example, BF 3 ⋅ Et 2 O is one of the most commonly used Lewis acid in synthetic chemistry [4] . In 1963, B(C 6 F 5 ) 3 (BCF) was first synthesized by Stone, Massey and Park, which was found to be a strong Lewis acid due to the strong electron‐withdrawing effects of the three aryl rings with fifteen fluorine atoms.…”