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

doi:10.1039/c8cc08227h

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 › peer-review

37 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 language	English
Pages (from-to)	13802-13804
Number of pages	3
Journal	Chemical Communications
Volume	54
Issue number	98
DOIs	https://doi.org/10.1039/c8cc08227h
Publication status	Published - 2018
Externally published	Yes

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

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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, 2018, p. 13802-13804.

Research output: Contribution to journal › Article › peer-review

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title = "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",

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.",

author = "Sina Witzel and Kohei Sekine and Matthias Rudolph and Hashmi, {A. Stephen K.}",

note = "Funding Information: Sina Witzel acknowledges the support from the Landesgra-duiertenf{\"o}rderung of the state of Baden-W{\"u}rttemberg. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

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AU - Sekine, Kohei

AU - Rudolph, Matthias

AU - Hashmi, A. Stephen K.

N1 - Funding Information: Sina Witzel acknowledges the support from the Landesgra-duiertenförderung of the state of Baden-Württemberg. Publisher Copyright: © The Royal Society of Chemistry. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

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AB - 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.

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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

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