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 journalArticle

2 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

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Desulfurization
Sulfhydryl Compounds
Gold
Light emitting diodes
Styrenes
Photocatalysis
Light sources
Amino acids
Styrene
Hydrogen
Polymers
Ligands
Amino Acids
Wavelength
Electrons

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Zhang, L., Si, X., Yang, Y., Witzel, S., Sekine, K., Rudolph, M., ... Hashmi, A. S. K. (2019). Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions. ACS Catalysis, 9(7), 6118-6123. https://doi.org/10.1021/acscatal.9b01368

Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions. / Zhang, Lumin; Si, Xiaojia; Yang, Yangyang; Witzel, Sina; Sekine, Kohei; Rudolph, Matthias; Rominger, Frank; Hashmi, A. Stephen K.

In: ACS Catalysis, Vol. 9, No. 7, 05.07.2019, p. 6118-6123.

Research output: Contribution to journalArticle

Zhang, L, Si, X, Yang, Y, Witzel, S, Sekine, K, Rudolph, M, Rominger, F & Hashmi, ASK 2019, 'Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions', ACS Catalysis, vol. 9, no. 7, pp. 6118-6123. https://doi.org/10.1021/acscatal.9b01368
Zhang, Lumin ; Si, Xiaojia ; Yang, Yangyang ; Witzel, Sina ; Sekine, Kohei ; Rudolph, Matthias ; Rominger, Frank ; Hashmi, A. Stephen K. / Reductive C-C Coupling by Desulfurizing Gold-Catalyzed Photoreactions. In: ACS Catalysis. 2019 ; Vol. 9, No. 7. pp. 6118-6123.
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AU - Rudolph, Matthias

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AU - Hashmi, A. Stephen K.

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