New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer

Sina Witzel, Kohei Sekine, Matthias Rudolph, A. Stephen K. Hashmi

Research output: Contribution to journal › Article

12 Citations (Scopus)

Abstract

The scope of photosensitizer-free visible light-driven gold-catalyzed cross-coupling was evaluated by a wide variety of organoboron and organosilicon species using four equivalents of aryldiazonium salts and (4-CF3-C6H4)3PAuCl in MeOH. In addition, a C(sp or sp2)-C(sp2) cross-coupling of organotrimethylsilanes and aryldiazonium salts was investigated. The reactions can be conducted under very mild reaction conditions, with a reduced amount of aryldiazonium salt (1.2 equiv.) by using a catalytic amount of Ph3PAuNTf2 in MeCN under irradiation with blue LEDs at room temperature.

Original languageEnglish
Pages (from-to)13802-13804
Number of pages3
JournalChemical Communications
Volume54
Issue number98
DOIs
Publication statusPublished - Jan 1 2018

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Photosensitizing Agents
Photosensitizers
Gold
Salts
Light emitting diodes
Irradiation
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer. / Witzel, Sina; Sekine, Kohei; Rudolph, Matthias; Hashmi, A. Stephen K.

In: Chemical Communications, Vol. 54, No. 98, 01.01.2018, p. 13802-13804.

Research output: Contribution to journal › Article

Witzel, S, Sekine, K, Rudolph, M & Hashmi, ASK 2018, 'New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer', Chemical Communications, vol. 54, no. 98, pp. 13802-13804. https://doi.org/10.1039/c8cc08227h
Witzel S, Sekine K, Rudolph M, Hashmi ASK. New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer. Chemical Communications. 2018 Jan 1;54(98):13802-13804. https://doi.org/10.1039/c8cc08227h
Witzel, Sina ; Sekine, Kohei ; Rudolph, Matthias ; Hashmi, A. Stephen K. / New transmetalation reagents for the gold-catalyzed visible light-enabled C(sp or sp2)-C(sp2) cross-coupling with aryldiazonium salts in the absence of a photosensitizer. In: Chemical Communications. 2018 ; Vol. 54, No. 98. pp. 13802-13804.
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