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Silver‐Mediated Oxidative Fluorotrifluoromethylation of Unactivated Alkenes
Author(s) -
Yu Wei,
Xu XiuHua,
Qing FengLing
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500027
Subject(s) - chemistry , selectfluor , iodobenzene , regioselectivity , trimethylsilane , trifluoromethylation , trifluoromethanesulfonate , dimethylformamide , organic chemistry , salt (chemistry) , medicinal chemistry , trifluoromethyl , catalysis , alkyl , solvent
An efficient regioselective fluorotrifluoromethylation of unactivated alkenes has been developed. The reaction of alkenes with (trifluoromethyl)trimethylsilane (TMSCF 3 ) and Selectfluor in the presence of silver trifluoromethanesulfonate (AgOTf), cesium fluoride (CsF), and iodobenzene diacetate [PhI(OAc) 2 ] in N , N ‐dimethylformamide (DMF) at −20 °C gave the corresponding fluorotrifluoromethylated products in moderate to good yields. The silver salt turns out to be crucial for this transformation.