Abstract
Organic azides have found wide application in various fields of science and technology. This review summarizes recently developed approaches to the direct, one-step synthesis of diverse organic azides utilizing hypervalent iodine reagents. The first part of review deals with the azidation using unstable azidoiodinanes generated in situ from common hypervalent iodine reagents (such as diacetoxyiodobenzene or iodosylbenzene) and a source of azide anion (TMSN3 or NaN3). The second part of review is dedicated to the application of stable azidobenziodoxoles as useful azidating reagents that allow selective direct azidation of C−H bonds or double carbon-carbon bonds under mild reaction conditions. The use of azidobenziodoxoles eliminates the main disadvantages of the traditional approaches to organic azides, such as the need in pre-functionalization of organic substrates and harsh reaction conditions. Synthetic application of azidobenziodoxoles made possible direct selective azidation of a plethora of organic substrates including complex molecules at the late synthetic stage.
Original language | English (US) |
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Article number | e202200754 |
Journal | European Journal of Organic Chemistry |
Volume | 2022 |
Issue number | 34 |
DOIs | |
State | Published - Sep 13 2022 |
Externally published | Yes |
Bibliographical note
Funding Information:This work was supported by the Russian Science Foundation (project No 21‐73‐20031). V.V.Z. is thankful to the National Science Foundation (CHE‐1759798) for support of his research program on hypervalent iodine chemistry at University of Minnesota Duluth.
Publisher Copyright:
© 2022 Wiley-VCH GmbH.
Keywords
- Azidation
- Azide
- Hypervalent compounds
- Hypervalent iodine
- Iodine