Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

Benz, Sebastian; Mareda, Jiri; Besnard, Céline; Sakai, Naomi; Matile, Stefan

doi:10.1039/C7SC03866F

Scientific article

English

Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

Contributors

Benz, Sebastian; Mareda, Jiri; Besnard, Céline; Sakai, Naomi

; Matile, Stefan

Published in

Chemical Science, vol. 8, no. 12, p. 8164-8169

Publication date

2017

Abstract

The benzodiselenazoles (BDS) introduced in this report fulfill, for the first time, all the prerequisites for non-covalent high-precision chalcogen-bonding catalysis in the focal point of conformationally immobilized σ holes on strong selenium donors in a neutral scaffold. Rational bite-angle adjustment to the long Se–C bonds was the key for BDS design. For the unprecedented BDS motif, synthesis of 12 analogs from o-xylene, crystal structure, σ hole variation strategies, optoelectronic properties, theoretical and experimental anion binding as well as catalytic activity are reported. Chloride binding increases with the depth of the σ holes down to KD = 11 μM in THF. Catalytic activities follow the same trend and culminate in rate enhancements for transfer hydrogenation of quinolines beyond 100 000.

UNIGE affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

UNIGE research groups

Groupe Matile

Citation (ISO format)

BENZ, Sebastian et al. Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength. In: Chemical Science, 2017, vol. 8, n° 12, p. 8164–8169. doi: 10.1039/C7SC03866F

Article (Published version)

CC BY

Identifiers

PID : unige:99706
DOI : 10.1039/C7SC03866F

Additional URL for this publication

http://xlink.rsc.org/?DOI=C7SC03866F

Journal ISSN

2041-6520

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480downloads

Creation

23/11/2017 12:11:00

First validation

23/11/2017 12:11:00

Update

13/10/2025 19:32:04

Status update

15/03/2023 02:28:50

Last indexation

16/02/2026 06:57:53

Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength

Contributors

Published in

Publication date

Abstract

UNIGE affiliation entities

UNIGE research groups

Citation (ISO format)

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Additional URL for this publication

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Technical informations

Creation

First validation

Update

Status update

Last indexation