Jump to main content
Jump to site search


Metal-encapsulation induces a highly regioselective Bingel–Hirsch reaction of the labile Y@Cs(6)-C82

Author affiliations

Abstract

The chemical properties of a prototypical labile mono-EMF, Y@Cs(6)-C82, have been systematically disclosed for the first time via a Bingel–Hirsch reaction. Three mono-adduct isomers, namely, 2a, 2b and 2c out of 44 possibilities for the Y@Cs(6)-C82 cage have been readily isolated, demonstrating surprisingly high regioselectivity. Crystallographic results of 2b unambiguously confirm its molecular structure with a singly bonded bromomalonate group attached onto the Cs(6)-C82 cage. Further computational results rationalize that the high regioselectivity is a consequence of the localization of high spin density and large frontier molecular orbital distribution on the corresponding carbon atoms stemming from the encapsulation of an yttrium atom into the low-symmetry Cs(6)-C82 cage with three-electron transfer from the metal to the cage.

Graphical abstract: Metal-encapsulation induces a highly regioselective Bingel–Hirsch reaction of the labile Y@Cs(6)-C82

Back to tab navigation

Supplementary files

Article information


Submitted
15 Sep 2020
Accepted
04 Oct 2020
First published
05 Oct 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Metal-encapsulation induces a highly regioselective Bingel–Hirsch reaction of the labile Y@Cs(6)-C82

W. Shen, L. Yang, B. Li, P. Jin, B. Yu, H. Cong, T. Akasaka and X. Lu, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC06226J

Social activity

Search articles by author

Spotlight

Advertisements