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Updated: Apr 22, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Heteroaromatic belts through fold-in synthesis: mechanistic insights into a macrocycle-templated Friedel-Crafts
Mateusz Kondratowicz1, Damian Myśliwiec, Tadeusz Lis
1Wydział Chemii, Uniwersytet Wrocławski ul. F. Joliot-Curie 14, 50-383 Wrocław (Poland) http://www.mstepien.edu.pl.
Abstract:
Direct alkylation of 9,9',9''-triethyl[2.2.2](2,7)carbazolophane with dimethoxymethane or paraformaldehyde affords a belt-like heteroaromatic structure, which forms as a kinetic product in acid-catalyzed condensations. In a competing, thermodynamically favored process, polymeric structures are formed by a largely regioselective condensation of stereochemically rigid "semi-belts". The relationship between these reactivity routes is rationalized in terms of strain release and differential reversibility of consecutive condensation steps.
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