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Selective N,O‐Addition of the TEMPO Radical to Conjugated Boryldienes
Author(s) -
Türkyilmaz Fatma,
Kehr Gerald,
Li Jun,
Daniliuc Constantin G.,
Tesch Matthias,
Studer Armido,
Erker Gerhard
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509114
Subject(s) - chemistry , nitrogen , borane , conjugated system , medicinal chemistry , molar ratio , radical , photochemistry , organic chemistry , catalysis , polymer
Abstract B(C 6 F 5 ) 2 ‐containing boryldienes 4 underwent the addition of two molar equivalents of TEMPO to give N,O‐bonded four‐membered heterocyclic products 7 . The reaction is a metal‐free example of the generation of reactive nitrogen‐centered TEMPO radical derivatives, in this case by the addition of TEMPO to the borane, followed by carbon–nitrogen bond formation and subsequent trapping of the resulting allyl radical by the second equivalent of TEMPO.