Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host

Manuel Petroselli; Julius Rebek Jr; Yang Yu

doi:10.1002/chem.202004953

Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host

Chemistry. 2021 Feb 15;27(10):3284-3287. doi: 10.1002/chem.202004953. Epub 2021 Jan 19.

Authors

Manuel Petroselli¹, Julius Rebek Jr², Yang Yu¹

Affiliations

¹ Center for Supramolecular Chemistry & Catalysis and Department of Chemistry, College of Science, Shanghai University, 99 Shang-Da Road, Shanghai, 200444, P. R. China.
² The Skaggs Institute for Chemical Biology and Department of Chemistry, The Scripps Research Institute for Chemical Biology and Department of Chemistry, 10550 North Torrey Pines Road, La Jolla, California, 92037, USA.

PMID: 33301606
DOI: 10.1002/chem.202004953

Abstract

Reduction of alkyl dihalide guests (2-5 and 7) with trialkylsilanes (R₃ SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥10³ m^-1 s^-1 ). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host-guest complexation rates to modulate the product selectivity in radical reactions.

Keywords: dynamic host; free radicals; radical reduction; supramolecular chemistry; water-soluble cavitand.

Abstract

Grants and funding