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Medientyp:
E-Artikel
Titel:
O2‐Mediated Oxidation of Aminoboranes through 1,2‐N Migration
Beteiligte:
Rauser, Marian;
Warzecha, Daniel P.;
Niggemann, Meike
Erschienen:
Wiley, 2018
Erschienen in:Angewandte Chemie International Edition
Sprache:
Englisch
DOI:
10.1002/anie.201803168
ISSN:
1433-7851;
1521-3773
Entstehung:
Anmerkungen:
Beschreibung:
<jats:title>Abstract</jats:title><jats:p>In analogy to the classical reaction of C−B bonds with peroxides, the first oxidative functionalization of aminoboranes through a 1,2‐N migration was realized. Readily available aliphatic nitro compounds are thereby transformed into N‐ and O‐functionalized hydroxylamines in a single synthetic operation. Addition of hazardous peroxides is avoided. Instead, the insertion of O<jats:sub>2</jats:sub>, as the terminal oxidant, into Zn−C bonds provides the necessary peroxides. The required zinc organyls, in turn, are formed through a boron‐to‐zinc exchange, from an organoboronic ester byproduct of the nitro‐to‐aminoborane transformation.</jats:p>