Iron‐Catalyzed Ring‐Opening/Allylation of Cycloalkyl Hydroperoxides with Allylic Sulfones DOI

Ming‐Hua Wang,

Jingqi Tao, Fan Yang

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2022, Номер 11(2)

Опубликована: Янв. 21, 2022

Abstract An efficient iron‐catalyzed allylation of cycloalkyl hydroperoxides with allylic sulfones via C−C bond cleavage is presented. This protocol provides an approach to a wide range distally allylated ketones good functional group tolerance and high regioselectivity under redox‐neutral conditions. Preliminary mechanistic study implies radical process might be involved in this reaction.

Язык: Английский

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges DOI
I. P. Beletskaya, Valentine P. Ananikov

Chemical Reviews, Год журнала: 2022, Номер 122(21), С. 16110 - 16293

Опубликована: Сен. 16, 2022

In the present review, we discuss recent progress in field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are considered─catalytic cross-coupling and catalytic addition reactions. The development advanced systems is aimed at improved catalyst efficiency, reduced loading, better cost environmental concerns, higher selectivity yields. important rise research efforts sustainability green chemistry areas critically assessed. paramount role mechanistic studies a new generation addressed, key achievements, problems, challenges summarized for this field.

Язык: Английский

Процитировано

202

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

Visible-light-induced C–H sulfenylation of quinoxalin-2(1H)-ones with disulfides by sustainable cerium catalysis DOI Creative Commons
Zhang Li-xi, Jingwen He, Pengfei Zhang

и другие.

Green Synthesis and Catalysis, Год журнала: 2022, Номер 4(3), С. 226 - 230

Опубликована: Апрель 12, 2022

Using visible light as energy to form free radicals has important synthetic value. A novel and efficient visible-light-mediated strategy been developed for the generation of thiobenzene through cerium-catalyzed activation disulfides. Through this photochemical reaction, various 3-sulfenylated quinoxalin-2(1H)-ones can be conveniently obtained in good yields with functional group tolerance. Our transformation provides an alternative that allows rapid access C3 sulfenylated a sustainable practical manner.

Язык: Английский

Процитировано

17

Visible light/copper catalysis enabled alkylation of silyl enol ethers with arylsulfonium salts DOI
Wenwen Cui,

Guoju Guo,

Yifei Wang

и другие.

Chemical Communications, Год журнала: 2023, Номер 59(42), С. 6367 - 6370

Опубликована: Янв. 1, 2023

An efficient protocol has been developed herein for the site-selective alkylation of silyl enol ethers with arylsulfonium salts giving access to valuable aryl alkyl thioethers under visible light conditions. Enabled by copper (I) photocatalysis, C-S bond can be selectively cleaved deliver C-centered radicals mild This method provides a straightforward approach utilize as sulfur sources synthesis thioethers.

Язык: Английский

Процитировано

11

Transition metal catalysed direct sulfanylation of unreactive C–H bonds: an overview of the last two decades DOI
Daniel S. Rampon, Diego Seckler, Eduardo Q. Luz

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(31), С. 6072 - 6177

Опубликована: Янв. 1, 2022

Transition metal catalysed C–S bond formation from unreactive C–H bonds is a remarkable tool in the late-stage functionalization of complex molecules. This review highlights significant advances and mechanistic analyses last two decades.

Язык: Английский

Процитировано

15

Copper catalyzed carbon-selenium bond formation via the coupling reaction of aryl halides, phenylboronic acid and Se DOI Creative Commons

Zeinab Shirvandi,

Nadya Ghorashi,

Amin Rostami

и другие.

Scientific Reports, Год журнала: 2025, Номер 15(1)

Опубликована: Апрель 16, 2025

This is the first report for C-Se bond formation involving reaction of aryl halides with arylboronic acid and selenium powder to synthesis unsymmetrical diaryl selenides in presence CuI as a homogeneous catalyst. A wide range react various substituted groups under optimal conditions provide desired good high yields. Also, same reactions were investigated M-MCF@Gua-Cu reusable magnetic nanocatalyst conditions. The catalyst allows simpler (easy work-up) greener methodology. In addition, advantages presented method include use acid/Se safe cost-effective arylselenating system, simplicity operation, green cheap solvent.

Язык: Английский

Процитировано

0

Photoinduced copper-catalyzed alkoxyl radical-triggered ring-expansion/aminocarbonylation cascade DOI
Jingqi Tao, Shuai Liu, Tianyu Zhang

и другие.

Chinese Chemical Letters, Год журнала: 2023, Номер 35(6), С. 109263 - 109263

Опубликована: Окт. 30, 2023

Язык: Английский

Процитировано

8

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

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

Iodine-Promoted Reductive Sulfenylation Using Ketones as Hydride Donors DOI
Yiping Duan,

Zhichao Guo,

Tiandong Zheng

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(8), С. 5851 - 5856

Опубликована: Апрель 8, 2024

Herein, an iodine-promoted reductive sulfenylation reaction of ketones with disulfides has been developed. This method provides approach for synthesizing unsymmetrical alkyl–alkyl and alkyl–aryl sulfides in a single step. Investigation the mechanism revealed that play dual role this process. They react to produce vinyl thioethers act as effective organic hydride donors, reducing number are formed situ. study expands range applications chemical synthesis.

Язык: Английский

Процитировано

2