Activation of O‑Electrophiles via Structural and Solvent Effects: SN2@O Reaction of Cyclic Diacyl Peroxides with Enol Acetates
The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C–O bond formation. Nucleophilic substitution at the oxygen atom of cyclic diacyl peroxides by enol acetates with the following deacylation leads to α-acyloxy...
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| Published in | Journal of organic chemistry Vol. 87; no. 21; pp. 13980 - 13989 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
04.11.2022
Amer Chemical Soc |
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| Abstract | The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C–O bond formation. Nucleophilic substitution at the oxygen atom of cyclic diacyl peroxides by enol acetates with the following deacylation leads to α-acyloxyketones with an appended carboxylic acid in 28–87% yields. The effect of fluorinated alcohols on the oxidative functionalization of enol acetates by cyclic diacyl peroxides was studied experimentally and computationally. Computational analysis reveals that the key step proceeds as a direct substitution nucleophilic bimolecular (SN2) reaction at oxygen (SN2@O). CF3CH2OH has a dual role in assisting in both steps of the reaction cascade: it lowers the energy of the SN2@O activation step by hydrogen bonding to a remote carbonyl and promotes the deacylation of the cationic intermediate. |
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| AbstractList | The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C-O bond formation. Nucleophilic substitution at the oxygen atom of cyclic diacyl peroxides by enol acetates with the following deacylation leads to α-acyloxyketones with an appended carboxylic acid in 28-87% yields. The effect of fluorinated alcohols on the oxidative functionalization of enol acetates by cyclic diacyl peroxides was studied experimentally and computationally. Computational analysis reveals that the key step proceeds as a direct substitution nucleophilic bimolecular (SN2) reaction at oxygen (SN2@O). CF3CH2OH has a dual role in assisting in both steps of the reaction cascade: it lowers the energy of the SN2@O activation step by hydrogen bonding to a remote carbonyl and promotes the deacylation of the cationic intermediate.The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C-O bond formation. Nucleophilic substitution at the oxygen atom of cyclic diacyl peroxides by enol acetates with the following deacylation leads to α-acyloxyketones with an appended carboxylic acid in 28-87% yields. The effect of fluorinated alcohols on the oxidative functionalization of enol acetates by cyclic diacyl peroxides was studied experimentally and computationally. Computational analysis reveals that the key step proceeds as a direct substitution nucleophilic bimolecular (SN2) reaction at oxygen (SN2@O). CF3CH2OH has a dual role in assisting in both steps of the reaction cascade: it lowers the energy of the SN2@O activation step by hydrogen bonding to a remote carbonyl and promotes the deacylation of the cationic intermediate. The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C-O bond formation. Nucleophilic substitution at the oxygen atom of cyclic diacyl peroxides by enol acetates with the following deacylation leads to alpha-acyloxyketones with an appended carboxylic acid in 28-87% yields. The effect of fluorinated alcohols on the oxidative functionalization of enol acetates by cyclic diacyl peroxides was studied experimentally and computationally. Computational analysis reveals that the key step proceeds as a direct substitution nucleophilic bimolecular (SN2) reaction at oxygen (SN2@O). CF3CH2OH has a dual role in assisting in both steps of the reaction cascade: it lowers the energy of the SN2@O activation step by hydrogen bonding to a remote carbonyl and promotes the deacylation of the cationic intermediate. The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C–O bond formation. Nucleophilic substitution at the oxygen atom of cyclic diacyl peroxides by enol acetates with the following deacylation leads to α-acyloxyketones with an appended carboxylic acid in 28–87% yields. The effect of fluorinated alcohols on the oxidative functionalization of enol acetates by cyclic diacyl peroxides was studied experimentally and computationally. Computational analysis reveals that the key step proceeds as a direct substitution nucleophilic bimolecular (SN2) reaction at oxygen (SN2@O). CF3CH2OH has a dual role in assisting in both steps of the reaction cascade: it lowers the energy of the SN2@O activation step by hydrogen bonding to a remote carbonyl and promotes the deacylation of the cationic intermediate. |
| Author | Alabugin, Igor V. Vil’, Vera A. Shuingalieva, Diana V. Krivoshchapov, Nikolai V. Kunitsyn, Artem Yu Gorlov, Evgenii S. Terent’ev, Alexander O. Medvedev, Michael G. |
| AuthorAffiliation | D. Mendeleev University of Chemical Technology of Russia Department of Chemistry and Biochemistry Russian Academy of Sciences N. D. Zelinsky Institute of Organic Chemistry |
| AuthorAffiliation_xml | – name: D. Mendeleev University of Chemical Technology of Russia – name: Russian Academy of Sciences – name: N. D. Zelinsky Institute of Organic Chemistry – name: Department of Chemistry and Biochemistry |
| Author_xml | – sequence: 1 givenname: Vera A. orcidid: 0000-0002-6847-6035 surname: Vil’ fullname: Vil’, Vera A. organization: Russian Academy of Sciences – sequence: 2 givenname: Evgenii S. surname: Gorlov fullname: Gorlov, Evgenii S. organization: Russian Academy of Sciences – sequence: 3 givenname: Diana V. surname: Shuingalieva fullname: Shuingalieva, Diana V. organization: D. Mendeleev University of Chemical Technology of Russia – sequence: 4 givenname: Artem Yu surname: Kunitsyn fullname: Kunitsyn, Artem Yu organization: Russian Academy of Sciences – sequence: 5 givenname: Nikolai V. surname: Krivoshchapov fullname: Krivoshchapov, Nikolai V. organization: Russian Academy of Sciences – sequence: 6 givenname: Michael G. orcidid: 0000-0001-7070-4052 surname: Medvedev fullname: Medvedev, Michael G. organization: Russian Academy of Sciences – sequence: 7 givenname: Igor V. orcidid: 0000-0001-9289-3819 surname: Alabugin fullname: Alabugin, Igor V. email: alabugin@chem.fsu.edu organization: Department of Chemistry and Biochemistry – sequence: 8 givenname: Alexander O. orcidid: 0000-0001-8018-031X surname: Terent’ev fullname: Terent’ev, Alexander O. email: terentev@ioc.ac.ru organization: Russian Academy of Sciences |
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| Keywords | MOLECULAR-ORBITAL METHODS NUCLEOPHILIC-SUBSTITUTION PHTHALOYL PEROXIDE AUGMENTED BASIS-SETS BETA-KETO-ESTERS FLUORINATED ALCOHOLS DENSITY-FUNCTIONAL THEORY ENANTIOSELECTIVE ALPHA-HYDROXYLATION ASYMMETRIC OXIDATION SYN-DIHYDROXYLATION |
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| Snippet | The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C–O bond... The reactions of O-electrophiles, such as organic peroxides, with carbon nucleophiles are an umpolung alternative to the common approaches to C-O bond... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Activation of O‑Electrophiles via Structural and Solvent Effects: SN2@O Reaction of Cyclic Diacyl Peroxides with Enol Acetates |
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