Radical Reactions in Cavitands Unveil the Effects of Affinity on Dynamic Supramolecular Systems.

Autor: Petroselli M; Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China.; Department of Physics, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China., Angamuthu V; Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China., Rahman FU; Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China., Zhao X; Department of Physics, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China., Yu Y; Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China., Rebek J Jr; Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science , Shanghai University , 99 Shang-Da Road , Shanghai 200444 , P. R. China.; The Skaggs Institute for Chemical Biology and Department of Chemistry , The Scripps Research Institute , 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2020 Feb 05; Vol. 142 (5), pp. 2396-2403. Date of Electronic Publication: 2020 Jan 27.
DOI: 10.1021/jacs.9b11595
Abstrakt: Radical reduction of alkyl halides and aerobic oxidation of alkyl aromatics are reported using water-soluble container compounds ( 1 and 2 ). The reductions involve α,ω-dihalides ( 4 - 8 and 10 ) with radical initiators in cavitand hosts with varied binding affinities. Product distributions lead to general guidelines for the use of dynamic supramolecular systems with fast reactions. The binding of guest substrates in the hosts must show high affinities ( K a > 10 3 M -1 ) to ensure that the reactions take place under confinement in the containers.
Databáze: MEDLINE
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