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Unlocking the N 2 Selectivity of Benzotriazoles: Regiodivergent and Highly Selective Coupling of Benzotriazoles with Allenes
Author(s) -
Xu Kun,
Thieme Niels,
Breit Bernhard
Publication year - 2014
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.201403682
Subject(s) - rhodium , selectivity , chemistry , benzotriazole , catalysis , reactivity (psychology) , coupling (piping) , medicinal chemistry , stereochemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , metallurgy
The rhodium‐catalyzed, highly N 2 ‐ and N 1 ‐selective coupling of benzotriazoles with allenes is reported. The exceptionally high N 2 and N 1 selectivities were achieved by using a rhodium(I)/DPEphos and rhodium(I)/JoSPOphos catalyst, respectively. This method permits the atom‐economic synthesis of valuable branched N 2 ‐ and N 1 ‐allylated benzotriazole derivatives and allows for preliminary studies of their reactivity.