Mild and General Access to Diverse 1H -Benzotriazoles via Diboron-Mediated N-OH Deoxygenation and Palladium-Catalyzed C-C and C-N Bond Formation

Advanced Synthesis & Catalysis
Venkateshwarlu GurramMahesh K Lakshman

Abstract

Benzotriazoles are a highly important class of compounds with broad-ranging applications in such diverse areas as medicinal chemistry, as auxiliaries in organic synthesis, in metallurgical applications, in aircraft deicing and brake fluids, and as antifog agents in photography. Although there are numerous approaches to N-substituted benzotriazoles, the essentially one general method to N-unsubstituted benzotriazoles is via diazotization of o-phenylenediamines, which can be limited by the availability of suitable precursors. Other methods to N-unsubstitued benzotriazoles are quite specialized. Although reduction of 1-hydroxy-1H-benzotriazoles is known the reactions are not particularly convenient or broadly applicable. This presents a limitation for easy access to and availability of diverse benzotriazoles. Herein, we demonstrate a new, broadly applicable method to diverse 1H-benzotriazoles via a mild diboron-reagent mediated deoxygenation of 1-hydroxy-1H-benzotriazoles. We have also evaluated sequential deoxygenation and Pd-mediated C-C and C-N bond formation as a one-pot process for further diversification of the benzotriazole moiety. However, results indicated that purification of the deoxygenation product prior to the Pd-med...Continue Reading

References

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Citations

Aug 9, 2016·Organic Letters·Kai YangQiuling Song
Aug 9, 2016·The Journal of Organic Chemistry·Zhi-Xin WangDong-Liang Mo
Nov 17, 2015·Angewandte Chemie·Justin Kim, Carolyn R Bertozzi
Sep 14, 2018·Organic & Biomolecular Chemistry·Sadaf AzeezJeyakumar Kandasamy
Dec 19, 2018·Advanced Synthesis & Catalysis·Magdalena R AndrzejewskaMahesh K Lakshman
Apr 29, 2021·Organic & Biomolecular Chemistry·Se Hyun KimJun Hee Lee
Nov 28, 2018·Organic Letters·Kyu Dong Kim, Jun Hee Lee

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