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Paper | Special issue | Vol 99, No. 2, 2019, pp.1183-1195
Published online, 15th February, 2019
DOI: 10.3987/COM-18-S(F)94
Synthesis of a Poly-Heterocyclic Tetra-Substituted Alkene via a Palladium-Catalyzed Four-Fold Domino Reaction for the Design of Polymeric Molecular Switches

Taukeer A. Khan and Lutz F. Tietze*

*Institute of Organic and Biomolecular Chemistry, University of Goettingen, Tammannstrasse 2, 37077 Goettingen, Germany

Abstract

A facile synthesis of a complex poly-heterocyclic tetrasubstituted alkene 4 with intrinsic helical chirality containing two acrylate moieties suitable for polymerization is described. Compound 4 can act as a molecular switch and was prepared via a palladium-catalyzed four-fold domino reaction including two Sonogashira reactions and two domino-carbopalladation/CH-activation reactions.