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

Jeremy H. Dworkin,

Zhuoxi M. Chen,

Kathleen C. Cheasty

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

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

Jeremy H. Dworkin,

Zhuoxi M. Chen,

Kathleen C. Cheasty

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

Процитировано

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