Facile Generation of Trideuteromethyl Radical from Alkylsilyl Peroxide and Subsequent Functionalization DOI
Jiahao Liu,

J. Nie,

Zhe Wang

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(11)

Опубликована: Авг. 23, 2024

Abstract Cu‐ and Fe‐ catalyzed trideuteromethylation reactions using alkylsilyl peroxide as trideuteromethyl radical precursor are reported. The was synthesized from acetone‐d6 in a three‐step sequence, the with various coupling partners afforded efficiently corresponding N−CD 3 , O−CD C−CD bond formation products. heptadeuteriopropylation prepared butyric acid‐d7 is also described.

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

1
Synthetic utility of functionalized alkylsilyl peroxides for Fe-catalyzed and visible-light-promoted radical transformation DOI Creative Commons
Jiahao Liu,

Shiyong Liu,

Zhe Wang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(13), С. 4757 - 4762

Опубликована: Янв. 1, 2024

α-Keto-, β-acetoxy- and β-amidoalkylsilyl peroxides are prepared from various precursors utilized for Fe-catalyzed visible-light-promoted radical functionalization with coupling partners under mild conditions a broad substrate scope.

Язык: Английский

Процитировано

4
Copper‐Catalyzed Asymmetric Radical 1,2‐Alkylesterification of 1,3‐Dienes with Cycloalkyl Hydroperoxides and Acids DOI
Tiantian Li, Ying Cheng, Wen‐Jing Xiao

и другие.

ChemCatChem, Год журнала: 2023, Номер 15(23)

Опубликована: Окт. 17, 2023

Abstract Transition‐metal‐catalyzed radical relay cross‐coupling reactions of 1,3‐dienes have recently emerged as one the most powerful methods for construction structurally diverse allylic compound in a single chemical step. However, there still has been limited success expanding substrate scope precursors and coupling partners, well exploring catalytic asymmetric variants. Herein, we report copper‐catalyzed enantioselective three‐component 1,2‐alkylesterification using cycloalkyl hydroperoxides carbonyl‐containing alkyl sources carboxylic acids O‐nucleophiles under mild redox‐neutral conditions. This protocol features broad good functional group tolerance with respect to each component, providing practical access variety distally keto‐functionalized esters high enantioselectivity. Mechanistic studies suggest involvement sequential C−O this reaction.

Язык: Английский

Процитировано

6
Carbon-Chain Elongation by Co-Catalyzed Selective C–C Bond Cleavage and Subsequent Silylperoxylation of Alkene Substrates DOI
Jiahao Xie, Terumasa Kato, Keiji Maruoka

и другие.

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 14754 - 14761

Опубликована: Сен. 20, 2024

Язык: Английский

Процитировано

1
A copper-catalyzed direct C(sp2)–H alkylsulfonylation of alkenes using alkylsilyl peroxides and DABCO·(SO2)2 DOI

Xueni Tian,

Lingling Chen,

Tong‐Hao Zhu

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4821 - 4826

Опубликована: Янв. 1, 2023

A copper-catalyzed C(sp 2 )–H alkylsulfonylation of alkenes using alkylsilyl peroxides as the alkyl radical precursors with insertion sulfur dioxide was developed, and shown to provide a convenient route diverse ( E )-alkylsulfonyl alkenes.

Язык: Английский

Процитировано

2
Facile Generation of Trideuteromethyl Radical from Alkylsilyl Peroxide and Subsequent Functionalization DOI
Jiahao Liu,

J. Nie,

Zhe Wang

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(11)

Опубликована: Авг. 23, 2024

Abstract Cu‐ and Fe‐ catalyzed trideuteromethylation reactions using alkylsilyl peroxide as trideuteromethyl radical precursor are reported. The was synthesized from acetone‐d6 in a three‐step sequence, the with various coupling partners afforded efficiently corresponding N−CD 3 , O−CD C−CD bond formation products. heptadeuteriopropylation prepared butyric acid‐d7 is also described.

Язык: Английский

Процитировано

0