Bioinspired Fe(II)‐Mediated Halogenative C−C Bond Activation of Ozonides: Temporary Installment of a Peroxide Bridge Allows Selective C−C Scissions for Replacement of a Carbonyl Group by a Halogen-Reference-Cited by-同舟云学术

Bioinspired Fe(II)‐Mediated Halogenative C−C Bond Activation of Ozonides: Temporary Installment of a Peroxide Bridge Allows Selective C−C Scissions for Replacement of a Carbonyl Group by a Halogen

Published:2023-10-27 Issue:23 Volume:365 Page:4190-4197
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Yaremenko Ivan A.¹^ORCID,Belyakova Yulia Yu.¹,Demina Arina A.¹,Radulov Peter S.¹^ORCID,Alabugin Igor V.²^ORCID,Terent'ev Alexander O.¹^ORCID

Affiliation:

1. N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky prosp. Moscow 119991 Russian Federation

2. Department of Chemistry and Biochemistry Florida State University Tallahassee Fl 32306 USA

Abstract

AbstractA selective reaction of bridged ozonides with Fe(II) salts proceeds through the sequence of O−O, C−C scissions and halogenation to form α‐halogen substituted δ‐ketoesters and δ‐diketones in 15–72% yields. The overall sequence shows how a temporary installation of a peroxide functionality can be used to replace the acyl group within an acetoacetic ester unit with a halogen.

Funder

Russian Science Foundation

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300881

Reference97 articles.

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