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
form
powder
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.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
存储类别
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
法规信息
新产品
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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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