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

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 Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2023, Volume: 365, Number: 23, Pages: 4190-4197 Pages count : 8 DOI: 10.1002/adsc.202300881

Authors

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

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, 119991 Russian Federation
2	Florida State University, UNITED STATES

A 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.

Yaremenko I. , Belyakova Y.Y. , Demina A.A. , Radulov P. , Alabugin I. , Terent'ev A.
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
Advanced Synthesis & Catalysis. 2023. V.365. N23. P.4190-4197. DOI: 10.1002/adsc.202300881 WOS Scopus OpenAlex

Web of science:	WOS:001090685200001
Scopus:	2-s2.0-85174973189
OpenAlex:	W4387663455

DB	Citing
OpenAlex	3
Scopus	2
Web of science	3