Synthesis of Sulfur Perfluorophenyl Compounds Using a Pentafluorobenzenesulfonyl Hypervalent Iodonium Ylide

A novel pentafluorobenzenesulfonyl hypervalent iodonium ylide 3 was designed and synthesized as a useful tool for the preparation of sulfur pentafluorophenyl compounds containing a C6F5S or C6F5SO2 unit. Electrophilic pentafluorophenylthiolation of enamines, formal [3+2] cycloaddition reaction of ni...

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Published inJournal of organic chemistry Vol. 82; no. 22; pp. 11939 - 11945
Main Authors Wang, Jiandong, Jia, Shichong, Okuyama, Kenta, Huang, Zhongyan, Tokunaga, Etsuko, Sumii, Yuji, Shibata, Norio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.11.2017
Amer Chemical Soc
Subjects
alkynes
chemical structure
Chemistry
Chemistry, Organic
cycloaddition reactions
enamines
Lewis acids
Lewis bases
nitriles
organic chemistry
Physical Sciences
Science & Technology
sulfur
TRIFLUOROMETHYLTHIOLATION
IN-VITRO BIOACTIVATION
ENAMINES
ESTROGEN-RECEPTOR LIGANDS
ASYMMETRIC HYDROGENATION
LIVER-MICROSOMES
FLUORINATION
EFFICIENT SULFENYLATION
MACROCYCLIZATION
ER-ALPHA
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.7b01908

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Summary:A novel pentafluorobenzenesulfonyl hypervalent iodonium ylide 3 was designed and synthesized as a useful tool for the preparation of sulfur pentafluorophenyl compounds containing a C6F5S or C6F5SO2 unit. Electrophilic pentafluorophenylthiolation of enamines, formal [3+2] cycloaddition reaction of nitriles and alkynes, and intramolecular SNAr cyclization were achieved using iodonium ylide 3. The fluoro-click reaction was also demonstrated using one of the products via an intermolecular SNAr reaction with heterocentered nucleophiles.
Bibliography:KAKEN
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b01908