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nov. 8 2019


Three new cis‐diquinoxaline spanned cavitands were successfully synthesized. These cis‐diphosphinated derivatives were applied in homogeneous gold‐catalyzed dimerization and hydration of alkynes as well as rhodium‐catalyzed styrene hydroformylation. The results were ranked with those obtained with their trans‐diphosphinated isomeric analogues. The structure‐activity relationship employing these two cavitands reveals that the cis‐ or trans‐positioning of the catalyst centers directly influences cooperation between the two metallic atoms to control catalytic activity, reaction profile, and product selectivity. This comparative study provides us an intellectual basis for future catalytic cavitand chemistry and homogeneous catalysis.

Graphical Abstract:

Synthesis of new cis‐typed bis‐phosphorus cavitands is described, including a description of their catalytic capability in transition‐metal‐catalyzed reactions. The catalysis of cis‐versions were compared to the corresponding trans‐isomeric bis‐phosphorus cavitands, which revealed that different shape of compartments gave different profile of reactivity and product distribution.


Reference :

Mami Inoue, Shinsuke Kamiguchi, Katto Ugawa, Shaima Hkiri, Jules Bouffard, David Sémeril, Tetsuo Iwasawa

Evaluation of the Catalytic Capability of cis‐ and trans‐Diquinoxaline Spanned Cavitands

EurJOC, first published: 3 September 2019 - DOI: https://doi-org.scd-rproxy.u-strasbg.fr/10.1002/ejoc.201901058

Contact chercheur :

David Sémeril, SOCAT, Institut de Chimie (UMR 7177).