Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions

Lumin Zhang, Xiaojia Si, Yangyang Yang, Sina Witzel, Kohei Sekine, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

[Au2(μ-dppm)2]Cl2-mediated photocatalysis reactions are usually initiated by ultraviolet A (UVA) light; herein, an unreported system using blue light-emitting diodes (LEDs) as excitation light source was found. The red shift of the absorption wavelength originates from the combination of [Au2(μ-dppm)2]Cl2 and ligand (Ph3P or mercaptan). On the basis of this finding, a gold-catalyzed reductive desulfurizing C-C coupling of electrophilic radicals and styrenes mediated by blue LEDs is presented, a coupling which cannot be efficiently accessed by previously reported methods. This mild and highly efficient C-C bond formation strategy uses mercaptans both as electron-deficient alkyl radical precursor as well as the hydrogen source. Two examples of amino acids have also been modified by using this strategy. Moreover, this methodology could be applied in polymer synthesis. Gram-scale synthesis and mechanistic insights into this transformation are also presented.

Original languageEnglish
Pages (from-to)6118-6123
Number of pages6
JournalACS Catalysis
Volume9
Issue number7
DOIs
Publication statusPublished - Jul 5 2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Fingerprint Dive into the research topics of 'Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions'. Together they form a unique fingerprint.

Cite this