Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 4, Pages 1935-1947Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02656
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Funding
- Russian Science Foundation [18-13-00027]
- Russian Science Foundation [18-13-00027] Funding Source: Russian Science Foundation
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Cross-dehydrogenative C-O coupling of N-hydroxyimides with ketones, esters, and carboxylic acids was achieved employing the di-tertbutyl peroxide as a source of free radicals and a dehydrogenating agent. The proposed method is experimentally simple and demonstrates the outstanding efficiency for the challenging CH substrates, such as unactivated esters and carboxylic acids. It was shown that N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO center dot radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C-O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the single-stage synthesis of commercial reagent (known as Baran aminating reagent precursor) from isobutyric acid and N-hydroxysuccinimide, whereas in the standard synthetic approach, four stages are necessary.
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