A Novel Approach to Functionalization of Aryl Azides through the Generation and Reaction of Organolithium Species Bearing Masked Azides in Flow Microreactors

Daisuke Ichinari; Yosuke Ashikari; Kyoko Mandai; Yoko Aizawa; Jun-Ichi Yoshida; Aiichiro Nagaki

doi:10.1002/anie.201912419

A Novel Approach to Functionalization of Aryl Azides through the Generation and Reaction of Organolithium Species Bearing Masked Azides in Flow Microreactors

Angew Chem Int Ed Engl. 2020 Jan 20;59(4):1567-1571. doi: 10.1002/anie.201912419. Epub 2019 Dec 6.

Authors

Daisuke Ichinari¹, Yosuke Ashikari¹, Kyoko Mandai¹, Yoko Aizawa¹, Jun-Ichi Yoshida², Aiichiro Nagaki¹

Affiliations

¹ Department of Synthetic and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto, 615-8510, Japan.
² National Institute of Technology, Suzuka College, Shiroko-cho, Suzuka, Mie, 510-0294, Japan.

PMID: 31733010
DOI: 10.1002/anie.201912419

Abstract

A novel straightforward method for aryl azides having functional groups based on generation and reactions of aryllithiums bearing a triazene group from polybromoarenes using flow microreactor systems was achieved. The present approach will serve as a powerful method in organolithium chemistry and open a new possibility in the synthesis of polyfunctional organic azides.

Keywords: azides; flow chemistry; microreactors; organolithium reagents.

Abstract

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