A Halogen-Bond Donor Catalyst for Templated Macrocyclization

Kevin Guillier (1) , Elsa Caytan (1) , Vincent Dorcet (1) , Florence Mongin (1) , Elise Dumont (2) , Floris Chevallier (2, 1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LC - Laboratoire de Chimie - UMR5182

A halogen-bond templated 11 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.

Keywords: organocatalysis; template synthesis; hydrogen transfer; halogen bonds; metathesis

Domains: Chemical Sciences

Kevin Guillier, Elsa Caytan, Vincent Dorcet, Florence Mongin, Elise Dumont, et al.. A Halogen-Bond Donor Catalyst for Templated Macrocyclization. Angewandte Chemie International Edition, 2019, 58 (42), pp.14940-14943. ⟨10.1002/anie.201908317⟩. ⟨hal-02303400⟩