Triazene-Activated Donor–Acceptor Cyclopropanes: Ring-Opening and (3 + 2) Annulation Reactions
Abdusalom A. Suleymanov, Eliott Le Du, Zhaowen Dong, Bastian Muriel, Rosario Scopelliti, Farzaneh Fadaei‐Tirani, Jérôme Waser, Kay Severin
Abstract
Donor-acceptor cyclopropanes substituted with 3,3-dialkyltriazenyl groups are described herein. The strong electron-donating character of the triazene renders the cyclopropanes highly reactive, allowing for catalyst-free ring-opening reactions with methanol and tetracyanoethylene under mild conditions. The triazene-substituted cyclopropanes could also be used as substrates in Lewis acid catalyzed (3 + 2) annulations with silyl enol ethers.
Topics & Concepts
ChemistryTetracyanoethyleneTriazeneAnnulationRing (chemistry)EnolCatalysisMedicinal chemistrySilylationLewis acids and basesMethanolOrganic chemistryPhotochemistryCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods