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Synthesis of Fluorinated Homoallylic Compounds by Fluoroalkyl Radical Mediated Ring Opening of Methylenecyclopropanes
Author(s) -
Xie Huajun,
Xu Bo
Publication year - 2016
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.201600380
Subject(s) - chemistry , ring (chemistry) , halide , medicinal chemistry , alcohol , copper , polymer chemistry , stereochemistry , organic chemistry
The fluoroalkyl (Rf) radical mediated ring opening of methylenecyclopropanes (MCPs) 1 and subsequent atom transfer were investigated. In the first part, a copper‐initiated radical reaction of Rf–X (X = I, Br) with MCP 1 gave homoallylic halides 2 in excellent yields. Similarly, radical reaction of the RfTMS/CsF/PhI(OCOR) 2 system with MCP 1 led to homoallylic alcohol esters 3 in moderate to good yields.
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