Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Photocatalyst in the Dual Catalytic Arylation of Alkyl Bis(catecholato)silicates

Tobias E Schirmer; Mehdi Abdellaoui; Aleksandr Savateev; Cyril Ollivier; Markus Antonietti; Louis Fensterbank; Burkhard König

doi:10.1021/acs.orglett.2c00529

Mesoporous Graphitic Carbon Nitride as a Heterogeneous Organic Photocatalyst in the Dual Catalytic Arylation of Alkyl Bis(catecholato)silicates

Org Lett. 2022 Apr 8;24(13):2483-2487. doi: 10.1021/acs.orglett.2c00529. Epub 2022 Mar 24.

Authors

Tobias E Schirmer¹, Mehdi Abdellaoui², Aleksandr Savateev³, Cyril Ollivier², Markus Antonietti³, Louis Fensterbank², Burkhard König¹

Affiliations

¹ Institute of Organic Chemistry, University of Regensburg, Universitätsstraße 31, Regensburg 93053, Germany.
² CNRS, Institut Parisien de Chimie Moléculaire -4 Place Jussieu, CC 229, Sorbonne Université, Paris Cedex 05 F-75252, France.
³ Department of Colloid Chemistry, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, Potsdam 14476, Germany.

PMID: 35324213
DOI: 10.1021/acs.orglett.2c00529

Abstract

Mesoporous graphitic carbon nitride (mpg-CN) is introduced as a heterogeneous photocatalyst to perform dual photoredox- and nickel-catalyzed cross-coupling reactions between alkyl bis(catecholato)silicates as radical precursors and aryl or alkenyl bromides. The synergy between this recyclable photocatalyst and the broadly applied homogeneous nickel complex [Ni(dtbbpy)Br₂] gives access to C(sp²)-C(sp³) cross-coupling products in a sustainable fashion. The recycled mpg-CN photocatalyst was analyzed by time-resolved emission spectroscopy and EPR spectroscopy.