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A Halogen‐Bond Donor Catalyst for Templated Macrocyclization
Author(s) -
Guillier Kévin,
Caytan Elsa,
Dorcet Vincent,
Mongin Florence,
Dumont Élise,
Chevallier Floris
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201908317
Subject(s) - halogen bond , chemistry , catalysis , halogen , metathesis , sodium borohydride , pyridine , methanol , ruthenium , transfer hydrogenation , combinatorial chemistry , tandem , salt metathesis reaction , hydrogen bond , alcohol , polymer chemistry , organic chemistry , molecule , materials science , alkyl , composite material , polymerization , polymer
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.