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Intermolecular Metal‐Free Cyclopropanation and Aziridination of Alkenes with XH <sub>2</sub> (X=N, C) by Thianthrenation**

Ming‐Shang Liu, Hai‐Wu Du, Jian‐Fang Cui, Wei Shu

2022Angewandte Chemie International Edition90 citationsDOI

Abstract

Abstract Three‐membered cyclic structures are widely existing in natural products and serve as enabling intermediates in organic synthesis. However, the efficient and straightforward access to such structures with diversity remains a formidable challenge. Herein, a general and practical protocol to aziridines and cyclopropanes synthesis using free XH 2 (X=C or N) with alkenes by thianthrenation is presented. This metal‐free protocol features the direct aziridination and cyclopropanation with unprotected XH 2 . Free sulfonamides, amides, carbamates, amines, and methylene with acidic protons, are good precursors, providing an attractive alternative for straightforward synthesis of aziridines and cyclopropanes from easily available starting materials.

Topics & Concepts

CyclopropanationIntermolecular forceChemistryCombinatorial chemistryMethyleneMetalStereochemistryOrganic chemistryCatalysisMoleculeSynthesis and Catalytic ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods