Unlocking the N2 Selectivity of Benzotriazoles: Regiodivergent and Highly Selective Coupling of Benzotriazoles with Allenes

The rhodium‐catalyzed, highly N2‐ and N1‐selective coupling of benzotriazoles with allenes is reported. The exceptionally high N2 and N1 selectivities were achieved by using a rhodium(I)/DPEphos and rhodium(I)/JoSPOphos catalyst, respectively. This method permits the atom‐economic synthesis of valua...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2014-07, Vol.53 (28), p.7268-7271
Main Authors: Xu, Kun, Thieme, Niels, Breit, Bernhard
Format: Article
Language:English
Subjects:
allenes
allylic compounds
benzotriazoles
heterocyles
homogeneous catalysis
Online Access:Get full text
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Summary:The rhodium‐catalyzed, highly N2‐ and N1‐selective coupling of benzotriazoles with allenes is reported. The exceptionally high N2 and N1 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 N2‐ and N1‐allylated benzotriazole derivatives and allows for preliminary studies of their reactivity. Ligand control: Exceptionally high N2 and N1 selectivities have been achieved in the rhodium‐catalyzed coupling of benzotriazoles with allenes by using DPEphos and JoSPOphos, respectively (see scheme). This method permits the atom‐economic synthesis of valuable branched N2‐ and N1‐allylated benzotriazole derivatives.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201403682