Synthesis 2023; 55(02): 263-271
DOI: 10.1055/a-1961-8237
short review

Halodiazirines as Valuable Reagents for the Synthesis of Halocyclo­propanes

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This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) (Discovery Grant RGPIN-2017-04272), the Fonds de recherche du Québec – Nature et technologies (FRQNT), Centre in Green Chemistry and Catalysis (CGCC), Strategic Cluster (FRQNT-2020-RS4-265155-CCVC), and Université Laval (UL) for financial support of our program. O.Mal. and M.M. thank MITACS for undergraduate Globalink research internships. O.Myk. and O.K. thank the Centre in Green Chemistry and Catalysis (CGCC) for undergraduate scholarships.


This short review is dedicated to Prof. Alain Krief on the occasion of his 80th birthday.

Abstract

Halodiazirines have emerged as very useful reagents in photochemically or thermally mediated cyclopropanation reactions with alkenes. This short review highlights the synthetic applications of these reagents as precursors of halocarbenes in transformations with various alkenes.

1 Introduction

2 Cyclopropanation of Aryl Halodiazirines

3 Tandem Reactions Using Aryl Halodiazirines

4 Cyclopropanation of Alkyl- and Benzyl-halodiazirines

5 Cyclopropanation of Other Halodiazirines

6 Reactions of Halodiazirines with Alkynes

7 Conclusion and Outlook



Publication History

Received: 06 October 2022

Accepted after revision: 17 October 2022

Accepted Manuscript online:
17 October 2022

Article published online:
16 November 2022

© 2022. Thieme. All rights reserved

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