Visible-Light Copper Nanocluster Catalysis for the C–N Coupling of Aryl Chlorides at Room Temperature

Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsatur...

Full description

Saved in:
Bibliographic Details
Published inJournal of the American Chemical Society Vol. 144; no. 27; pp. 12052 - 12061
Main Authors Sagadevan, Arunachalam, Ghosh, Atanu, Maity, Partha, Mohammed, Omar F., Bakr, Osman M., Rueping, Magnus
Format Journal Article
LanguageEnglish
Published American Chemical Society 13.07.2022
Subjects
ambient temperature
catalysts
catalytic activity
cross-coupling reactions
heterocyclic nitrogen compounds
industry
irradiation
Lewis bases
light
surface area
Online AccessGet full text

Cover

More Information
Summary:Activation of aryl chlorides in cross-coupling reactions is a long-standing challenge in organic synthesis that is of great interest to industry. Ultrasmall (<3 nm), atomically precise nanoclusters (NCs) are considered one of the most promising catalysts due to their high surface area and unsaturated active sites. Herein, we introduce a copper nanocluster-based catalyst, [Cu61(StBu)26S6Cl6H14] (Cu61NC) that enables C–N bond-forming reactions of aryl chlorides under visible-light irradiation at room temperature. A range of N-heterocyclic nucleophiles and electronically and sterically diverse aryl/hetero chlorides react in this new Cu61NC-catalyzed process to afford the C–N coupling products in good yields. Mechanistic studies indicate that a single-electron-transfer (SET) process between the photoexcited Cu61NC complex and aryl halide enables the C–N-arylation reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.2c02218