In:
Angewandte Chemie, Wiley, Vol. 133, No. 29 ( 2021-07-12), p. 16064-16070
Abstract:
We describe the first electrochemical activation of D–A cyclopropanes and D–A cyclobutanes leading after C(sp 3 )−C(sp 3 ) cleavage to the formation of highly reactive radical cations. This concept is utilized to formally insert molecular oxygen after direct or DDQ‐assisted anodic oxidation of the strained carbocycles, delivering β‐ and γ‐hydroxy ketones and 1,2‐dioxanes electrocatalytically. Furthermore, insights into the mechanism of the oxidative process, obtained experimentally and by additional quantum‐chemical calculations are presented. The synthetic potential of the reaction products is demonstrated by diverse derivatizations.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v133.29
DOI:
10.1002/ange.202101477
Language:
English
Publisher:
Wiley
Publication Date:
2021
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505868-5
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506609-8
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514305-6
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505872-7
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1479266-7
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505867-3
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506259-7
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