A Halogen‐Bond Donor Catalyst for Templated Macrocyclization. Issue 42 (5th September 2019)

• Record Type: Journal Article
• Authors: Guillier, Kévin; Caytan, Elsa; Dorcet, Vincent; Mongin, Florence; Dumont, Élise; Chevallier, Floris
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 42(2019)
• Page Start: 14940
• Page End: 14943
• Publication Date: 2019-09-05
• Subjects: halogen bonds -- hydrogen transfer -- metathesis -- organocatalysis -- template synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201908317
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A halogen‐bond templated 1:1 macrocyclization in solution is reported. Tetra(iodoperfluorophenyl) ethers were used as halogen‐bonded exotemplates in a substoichiometric amount (5 mol %). Pyridine‐containing macrocyclic architectures were formed by ruthenium‐catalyzed tandem metathesis/transfer hydrogenation sequence using sodium borohydride and methanol as non‐dihydrogen hydrogen source. The halogen‐bonded stabilization energies were analyzed relying on density functional theory. Abstract : Iodoperfluorophenyl ethers were used as exotemplates in a substoichiometric amount to perform a halogen‐bond templated 1:1 macrocyclization of pyridine derivatives through a tandem olefin metathesis/transfer hydrogenation.