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ALD00424

Sigma-Aldrich

2-Naphthalenyl ester fluorosulfuric acid

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About This Item

Empirical Formula (Hill Notation):
C10H7FO3S
CAS Number:
141694-39-5
Molecular Weight:
226.22
UNSPSC Code:
12352100
PubChem Substance ID:
329772675
NACRES:
NA.22

form

powder

SMILES string

O=S(OC1=CC=C2C(C=CC=C2)=C1)(F)=O

InChI

1S/C10H7FO3S/c11-15(12,13)14-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H

InChI key

IJQQGAGYVGLLJL-UHFFFAOYSA-N

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General description

2-Naphthalenyl ester fluorosulfuric acid is a diaryl fluorosulfate (diaryl-OSO2F). It can be synthesized with 99% yield from the reaction between phenol and sulfuryl fluoride in the presence of triethylamine. It undergoes Suzuki-Miyaura reaction with aryl boronic acid in the presence of Pd(OAc)2 and Et3N to afford the corresponding biaryl derivative.[1]

Application

The following aryl fluorosulfate can be utilized as a cross-coupling partner in Suzuki-Miyaura reactions. The standard reaction conditions for these palladium-catalyzed C-C bond formations are ligand-free and can be performed in water, at room temperature and are not air sensitive.

Other Notes

Palladium-Catalyzed, Ligand-Free Suzuki Reaction in Water Using Aryl Fluorosulfates

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Qiaobin Liang et al.
Organic letters, 17(8), 1942-1945 (2015-04-10)
Aryl fluorosulfates were prepared by a simple method and employed as coupling partners in the Suzuki-Miyaura reaction. The cross-coupling reactions were performed in water under air at room temperature without ligands or additives such as surfactants or phase-transfer reagents and

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