ALD00424
2-Naphthalenyl ester fluorosulfuric acid
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About This Item
Empirical Formula (Hill Notation):
C10H7FO3S
CAS Number:
Molecular Weight:
226.22
UNSPSC Code:
12352100
PubChem Substance ID:
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.
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Skin Corr. 1B
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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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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