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Inherent Oxygen Preference in Enolate Monofluoromethylation and a Synthetic Entry to Monofluoromethyl Ethers
Author(s) -
Nomura Yoshinori,
Tokunaga Etsuko,
Shibata Norio
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006218
Subject(s) - electrophile , alkylation , preference , chemistry , oxygen atom , selectivity , salt (chemistry) , computer science , contrast (vision) , organic chemistry , information retrieval , combinatorial chemistry , molecule , mathematics , artificial intelligence , statistics , catalysis
Expect the unexpected : The self‐stable salts 1 , X=OTf, PF 6 , x =2, y =1, developed for electrophilic monofluoromethylation showed inherent selectivity for the O‐alkylation of enolates, thus providing access to monofluoromethyl ethers, which are difficult to obtain by the direct electrophilic fluoromethylation of alcohols. Salt 1 , X=BF 4 , x =0, y =3, in contrast leads to C‐alkylated products.