Advances in radical peroxidation with hydroperoxides DOI Creative Commons
Oleg V. Bityukov,

Pavel Yu. Serdyuchenko,

Andrey S. Kirillov

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2959 - 3006

Published: Nov. 18, 2024

Organic peroxides have become sought-after functionalities, particularly following the multi-tone consumption in polymer production and success medicinal chemistry. The selective introduction of a peroxide fragment at different positions on target molecule is priority modern reaction design. pioneering Kharasch-Sosnovsky peroxidation became basic universal platform for development methods, with its great potential rapid generation complexity due to ability couple resulting free radicals wide range partners. This review discusses recent advances radical Kharasch-type functionalization organic molecules OOR including free-component couplings. discussion has been structured by type substrate peroxidation: C(sp

Language: Английский

Hydrodealkenylative C(sp3)–C(sp2) Bond Fragmentation Using Isayama–Mukaiyama Peroxidation DOI

Jeremy H. Dworkin,

Zhuoxi M. Chen,

Kathleen C. Cheasty

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

Advancements in radical capture strategies have expanded the range of products accessible from alkenes through dealkenylative synthesis. These methods, however, are still limited, as they rely on ozonolysis to generate key peroxide intermediates alkenes. Ozonolysis has several limitations. It is not compatible with containing electron-rich aromatics. also inapplicable certain alkene substitution patterns context Additionally, it struggles sterically hindered alkenes, internal nucleophiles and electrophiles, allylic alcohols. In this paper, using Isayama-Mukaiyama peroxidation (IMP), we address limitations rescue previously inaccessible substrates broaden applicability functionalization. particular, apply IMP hydrodealkenylation describe a novel hydrogenation condition─employing catalytic [FeIII], benzenethiol, γ-terpinene refluxing methanol─to resolve β-scission issues associated IMP-generated alkyl silylperoxides.

Language: Английский

Citations

1
Advances in radical peroxidation with hydroperoxides DOI Creative Commons
Oleg V. Bityukov,

Pavel Yu. Serdyuchenko,

Andrey S. Kirillov

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 2959 - 3006

Published: Nov. 18, 2024

Organic peroxides have become sought-after functionalities, particularly following the multi-tone consumption in polymer production and success medicinal chemistry. The selective introduction of a peroxide fragment at different positions on target molecule is priority modern reaction design. pioneering Kharasch-Sosnovsky peroxidation became basic universal platform for development methods, with its great potential rapid generation complexity due to ability couple resulting free radicals wide range partners. This review discusses recent advances radical Kharasch-type functionalization organic molecules OOR including free-component couplings. discussion has been structured by type substrate peroxidation: C(sp

Language: Английский

Citations

2