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

• Published in: Angewandte Chemie International Edition Vol. 59; no. 4; pp. 1567 - 1571
• Main Authors: Ichinari, Daisuke, Ashikari, Yosuke, Mandai, Kyoko, Aizawa, Yoko, Yoshida, Jun‐ichi, Nagaki, Aiichiro
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 20.01.2020; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Aromatic compounds; azides; Azides (organic); Chemistry; Chemistry, Multidisciplinary; flow chemistry; Functional groups; Microreactors; Organic chemistry; organolithium reagents; Physical Sciences; Science & Technology; REACTORS; ACTIVATION; REAGENTS; AROMATIC RING; azides; ORGANIC AZIDES; SPACE INTEGRATION; microreactors; CLICK-CHEMISTRY; LITHIATION; EFFICIENT; DERIVATIVES; flow chemistry; organolithium reagents
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201912419

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. Beneath the mask: A novel and straightforward method for synthesizing aryl azides bearing a variety of functional groups by using a flow microreactor system was developed. This strategy is based on the generation and reaction of aryllithium species bearing a triazene as a masked azide group.