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Bench‐Stable S ‐(Monofluoromethyl)sulfonium Salts: Highly Efficient C ‐ and O ‐Regioselective Monofluoromethylation of 1,3‐Dicarbonyl Compounds
Author(s) -
Qin WenBing,
Liu JianJian,
Huang Zhongyan,
Li Xin,
Xiong Wei,
Chen JiaYi,
Liu GuoKai
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000998
Subject(s) - regioselectivity , chemistry , sulfonium , reagent , electrophile , reactivity (psychology) , organic chemistry , reaction conditions , combinatorial chemistry , medicinal chemistry , salt (chemistry) , catalysis , medicine , alternative medicine , pathology
The new bench‐stable electrophilic monofluoromethylating reagents, S ‐(monofluoromethyl)‐S‐phenyl‐S‐(2,4,6‐trialkoxyphenyl)sulfonium salts, were successfully developed, which were readily prepared from inexpensive starting materials 1,3,5‐trimethoxybenzene and monofluoromethyl phenyl sulfoxides. The reactivity of these reagents was demonstrated through the C ‐ and O ‐regioselective monofluoromethylation of 1,3‐dicarbonyl compounds. Employing this reagent, a wide range of β‐keto esters easily underwent O ‐regioselective monofluoromethylation reaction to afford their corresponding O ‐monofluoromethylated products in good to excellent yields under mild reaction conditions. Contrastively, various malonates were smoothly transferred into their corresponding C ‐monofluoromethylated products in good to excellent yields under the standard reaction conditions.