Behavior of morpholine and its trimethylsilyl derivative in reactions with trimethylsilyl isocyanate DOI Creative Commons
Л. О. Белова,

N. A. Golub,

M. V. Pletneva

и другие.

Fine Chemical Technologies, Год журнала: 2022, Номер 17(5), С. 377 - 383

Опубликована: Ноя. 19, 2022

Objectives . To study the patterns of behavior morpholine and its trimethylsilyl derivative in reactions with isocyanate. Methods The employed infrared nuclear magnetic resonance spectroscopy, as well elemental analysis. Results formation mixtures tautomeric forms silicon-containing urea—N-(trimethylsilyl) morpholine-4-carboxamide trimethylsilylmorpholine-4-carboximidoate—was established. Conclusions It is shown that composition structure resulting products are determined both by presence a substituent at nitrogen atom type isocyanate used. Unlike morpholine, itself reacts to form mixture forms.

Язык: Английский

When all C–C breaks LO–Ose DOI Creative Commons

Jeremy H. Dworkin,

Brady W. Dehnert,

Ohyun Kwon

и другие.

Trends in Chemistry, Год журнала: 2023, Номер 5(3), С. 174 - 200

Опубликована: Фев. 14, 2023

Organic peroxides are becoming popular intermediates for novel chemical transformations. The weak O-O bond is readily reduced by transition metals, including iron and copper, to initiate a radical cascade process that breaks C-C bonds. Great potential exists the rapid generation of complexity, originating from ability couple resulting free radicals with wide range partners. First, this review article discusses history synthesis organic peroxides, providing context necessary understand methodology. Then, it highlights 91 examples recent applications functionalization bonds accessed through metal-mediated reduction peroxides. Finally, we provide some comments about safety when working

Язык: Английский

Процитировано

18

Nickel-Catalyzed Radical Ring-Opening Phosphorylation of Cycloalkyl Hydroperoxides Leading to Distal Acylphosphine Oxides DOI

Yue Ying,

Ziyi Ye,

An Wang

и другие.

Organic Letters, Год журнала: 2023, Номер 25(6), С. 928 - 932

Опубликована: Фев. 2, 2023

A facile and efficient nickel-catalyzed C-C bond cleavage/phosphorylation of various cycloalkyl hydroperoxides was developed. This radical ring-opening strategy provided practical access to structurally diverse distal ketophosphine oxides in one pot through concurrent C═O/C-P formation with high atom economy under mild room temperature base-free conditions.

Язык: Английский

Процитировано

6

Visible light-promoted alkylation of electron-deficient alkenes with alkylsilyl peroxides DOI
Shuji Nagano, Natsumi Maeda, Terumasa Kato

и другие.

Tetrahedron Letters, Год журнала: 2023, Номер 122, С. 154486 - 154486

Опубликована: Апрель 28, 2023

Язык: Английский

Процитировано

6

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

Photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade DOI
Jinhua Zhang,

Hong-Jie Miao,

Xin Hong

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(40), С. 5334 - 5337

Опубликована: Янв. 1, 2024

A photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade is developed. The protocol features broad substrate scope and excellent functional group compatibility.

Язык: Английский

Процитировано

2

Synthesis of 1,3‑dicarbonyl compounds bearing hetero-substituted α-quaternary carbon via Fe(II)-catalyzed alkylation with alkylsilyl peroxides DOI
Mi Zhou,

Hanbin Lu,

Zhe Wang

и другие.

Tetrahedron Letters, Год журнала: 2022, Номер 110, С. 154176 - 154176

Опубликована: Окт. 7, 2022

Язык: Английский

Процитировано

8

p-Methoxybenzyl-Radical-Promoted Chemoselective Protection of sec-Alkylamides DOI

Jingwen Jia,

Terumasa Kato, Keiji Maruoka

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(4), С. 2575 - 2582

Опубликована: Фев. 2, 2023

The hitherto difficult site-selective p-methoxybenzylation of secondary amides using p-methoxybenzylated alkylsilyl peroxides as a novel agent under copper catalysis is reported. reaction proceeds mild conditions in highly chemoselective manner. This approach was successfully applied to the peptides.

Язык: Английский

Процитировано

4

Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C–C Bond Cleavage/Cyclization of N-Functionalized Acrylamides DOI
Yingjie Ma,

Zi-Hang Yuan,

Pin Gao

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(14), С. 9927 - 9940

Опубликована: Июль 11, 2023

An array of redox-neutral alkylation/cyclization cascade reactions N-functionalized acrylamides with cycloalkyl hydroperoxides were achieved via the alkoxyl radical-triggered C-C bond cleavage. Through adjusting radical acceptors on N atom, a variety keto-alkylated chain-containing azaheterocycles, including indolo[2,1-a]isoquinolin-6(5H)-ones, quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridines constructed by one-pot procedure good yields excellent functional group tolerance.

Язык: Английский

Процитировано

4

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