Recent Advances in the Intramolecular Reactions of Epoxides with Arenes and Heteroarenes

Abstract

Over the years, the reactions and applications of epoxides have attracted the attention of many research groups. Intramolecular reactions of epoxides with arenes, termed epoxide-arene cyclizations (EACs) in this Focus Review,a re the intramolecular CÀCb ond-formingr eactions of arenesw ith tethered epoxides and represent ap articular type of epoxide-derivatization reactions. EACs have been successfully appliedt ot he synthesis of various benzo-fused carbo-and heterocyclesa sr eliable CÀCb ond-formingr eactions with complete atom economy.I nt his Focus Review,r esults in the literatures ince 2011o nt he development of EACs are presented.D ifferent aspects of substrate reactivities, the regio-and stereochemical outcomeso ft hese reactions, andtheir proposed mechanismsare discussed.Scheme1.Majorp athways for utilizingE ACs in the synthesis of benzo-fused carbo-and heterocycles.[a] Dr.The ORCID identification number(s) for the author(s) of this articlecan be found under http://dx.H is current research focuses on methodological advances in epoxide/aziridine chemistry and their applications in the synthesis of natural products and natural-product-like molecules.Scheme2.InCl 3 (10 mol %)-catalyzed synthesis of cis-2-hydroxyindenones through aFriedel-Crafts EAC reaction.

Recent Advancements in Typical Friedel–Crafts Alkylation Reactions Focused on Targeting Arene Nucleophiles

“…173 Furthermore, Das reviewed FC intramolecular C-C bondforming reactions of arene or heteroarene nucleophiles with tethered epoxides starting materials. 174 In 2010, Qu and Li studied the FC alkylation of arene nucleophiles with epoxides promoted by HFIP or water under refluxing conditions. 17g Similarly, Zhang and co-workers, in 2012, reported an efficient synthesis of isochromanones and isoquinolines via Lewis acid catalyzed tandem epoxide ring opening FC cyclization.…”

One-pot synthesis of epoxides from benzyl alcohols and aldehydes

“…Common examples of their utility include stereospecific ring opening [5–7], rearrangements into carbonyls [8–17], and application to cascade or domino reactions [18–19]. More recently, our group has used benzyl epoxides for the photoredox generation of carbonyl ylides which are leveraged in the synthesis of cyclic ethers [20].…”