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

Arunachalam Sagadevan, Atanu Ghosh, Partha Maity, Omar F. Mohammed, Osman M. Bakr*, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)12052-12061
Number of pages10
JournalJournal of the American Chemical Society
Volume144
Issue number27
DOIs
StatePublished - Jul 13 2022

Bibliographical note

Funding Information:
This work was financially supported by the King Abdullah University of Science and Technology (KAUST), Saudi Arabia, Office of Sponsored Research (FCC/1/1974).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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