Fe-catalyzed ring-opening reactions of siloxy cyclopropanes with alkenes and TBHP: Synthesis of 4-ester peroxides

Lou, Chenhao; Lv, Leiyang; Li, Zhiping

doi:10.1016/j.jorganchem.2022.122467

Cited by 7 publications

(3 citation statements)

References 51 publications

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“…In accordance with some literature reports on the Fe-catalyzed ring opening of cyclopropanols, 8 the probable involvement of a radical species was suspected and to confirm this, TEMPO was used as a radical scavenger. Under the standard reaction condition, the product formation was significantly suppressed, which indicates the involvement of a radical species in an intermediate step of the catalytic cycle.…”

supporting

confidence: 66%

“…Based on the control experiments and literature precedence, 8,9 a plausible mechanism for the Fe( ii )-catalyzed ring opening of bicyclo[n.1.0]alkanols and their tandem 1,6-conjugate addition to p -QMs is depicted in Scheme 4. The catalytic cycle initiates with a single electron reduction of Fe( ii ) to Fe( i ) via a Proton Coupled Electron Transfer pathway (PCET).…”

mentioning

confidence: 99%

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Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Jha,

Mondal,

Kapur

2023

Chem. Commun.

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supporting

confidence: 66%

mentioning

confidence: 99%

Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Jha,

Mondal,

Kapur

2023

Chem. Commun.

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“…Loh’s group investigated the bifunctionalization of olefins and using Fe as a catalyst. The target compound was synthesized from peroxides. ,− In 2019, Yang’s group developed the four-component free radical bifunctionalization and alkylated peroxidation reaction strategy for two different olefins with aldehyde and TBHP, facilitated by salen . In addition to this, manganese is also used as a catalyst in the synthesis of peroxides .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α/β-Aromatic Peroxy Thiols Mediated by Iodine Source

Zhang,

Liu,

Abdukerem

et al. 2024

J. Org. Chem.

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Peroxygenated compounds have wide applications in various fields, including chemistry, pharmaceutical chemistry, medicine, and materials science. However, there is still a need for more efficient and environmentally friendly synthesis methods for such compounds. Herein, we investigated the two-step, one-pot, regioselective synthesis of α/β-aromatic peroxy thiols. We explored various substrates and solvents for the reaction and identified the optimal reaction conditions. We successfully obtained several peroxy thiols in moderate to good yields via the selective generation of effective intermediates of iodoalkyl peroxides at room temperature without the need for metal catalysts.

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Stereoselective Photoredox Catalyzed (3+3) Dipolar Cycloaddition of Nitrone with Aryl Cyclopropane

Xu,

Gao,

Pan

et al. 2023

Angewandte Chemie

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By resorting to the principle of remote activation, we herein demonstrate the first photoredox catalyzed (3+3) dipolar cycloaddition of nitrones with aryl cyclopropanes. Key to the fidelity of the reaction resides in a facile manner of substrate activation by single‐electron transfer (SET) oxidation with photoredox catalysis, and the reaction takes place through a stepwise cascade encompassing a three‐electron‐type nucleophilic substitution triggered cyclopropane ring‐opening and a diastereoselective 6‐endo‐trig radical cyclization manifold. The reaction proceeds under mild conditions with excellent regio‐ and stereoselectivity, nicely complementing the well‐developed Lewis acid catalyzed cycloaddition of donor‐acceptor cyclopropanes. Other merits of the protocol include wide scope of aryl cyclopropanes with diversified substitution patterns and good functional‐group compatibility. A mechanism involving an aryl radical cation promoted remote activation mode was also proposed and supported by mechanistic experiments.

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Fe-catalyzed ring-opening reactions of siloxy cyclopropanes with alkenes and TBHP: Synthesis of 4-ester peroxides

Cited by 7 publications

References 51 publications

Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Site-selective ring opening of bicyclo[n.1.0]alkanols: an Fe(ii)-catalyzed 1,6-conjugate addition to p-quinone methides

Synthesis of α/β-Aromatic Peroxy Thiols Mediated by Iodine Source

Stereoselective Photoredox Catalyzed (3+3) Dipolar Cycloaddition of Nitrone with Aryl Cyclopropane

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