Rapid and scalable ruthenium catalyzed meta-C–H alkylation enabled by resonant acoustic mixing DOI Creative Commons
Arnab Dey, Rajesh Kancherla, Kuntal Pal

и другие.

Communications Chemistry, Год журнала: 2024, Номер 7(1)

Опубликована: Дек. 18, 2024

Synthetic chemistry approaches for direct C–H bond alkylation offers a promising alternative to traditional functional-group-centered strategies which often involve multi-step procedures and may suffer from variety of challenges including scalability. Here, we introduce resonant mixing as an efficient method meta-C–H arenes using Ru-catalyst, avoiding the need bulk solvents, external temperature, or light. The described methodology is highly rapid, enabling multigram-scale synthesis meta-alkylation products within short reaction time achieving very high turnover frequency. operates via radical mechanism characterized by its mild conditions, substrate compatibility, exceptional meta-selectivity, all while significantly reducing times. authors acoustic Ru-catalyst mechanism,

Язык: Английский

Ruthenium(II)-Catalyzed Remote C–H Alkylation of Arenes Using Diverse N-Directing Groups through Aziridine Ring Opening DOI

Hongyan Lan,

Yingzhen Liu,

Lutz Ackermann

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Сен. 12, 2024

An efficient approach for the remote C-H alkylation of arenes, employing a variety N-directing groups is described. This method facilitates straightforward synthesis valuable phenylethylamine derivatives by exclusively cleaving benzylic C-N bond in aziridines. Furthermore, these products can easily remove protecting groups, resulting meta-substituted compounds, such as amines and ketones, which hold significance synthetic chemistry.

Язык: Английский

Процитировано

5

Merging Visible Light Photocatalysis and P(III)‐Directed C−H Activation by a Single Catalyst: Modular Assembly of P‐Alkyne Hybrid Ligands DOI
Jiang Wang,

Xiuxiu Yang,

Lin Lin

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(47)

Опубликована: Окт. 10, 2023

Metal-catalyzed C-H activation strategies provide an efficient approach for synthesis by minimizing atom, step, and redox economy. Developing milder, greener, more effective protocols these is always highly desirable to the scientific community. In this study, utilization of a single rhodium complex enabled visible-light-induced late-stage biaryl-type phosphines with alkynyl bromides, employing inherent phosphorus atoms as directing groups. This chemistry combines P(III)-directed visible light photocatalysis, under exogenous photosensitizer-free conditions, offering unique platform ligand design preparation. Furthermore, study also explores asymmetric catalysis coordination resulting P-alkyne hybrid ligands specific transition metals. Experimental results density functional theory calculations demonstrate mechanistic intricacies transformation.

Язык: Английский

Процитировано

10

Photo‐Induced Ruthenium‐Catalyzed C−H Arylation Polymerization at Ambient Temperature DOI Creative Commons
Takuya Michiyuki, Isaac Maksso, Lutz Ackermann

и другие.

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(25)

Опубликована: Апрель 18, 2024

Transition metal-catalyzed C-H arylation polymerization (CHAP) is an attractive tool for constructing π-conjugated polymers in a sustainable manner. However, the existing methods primarily rely on palladium catalysis, which usually entails harsh reaction conditions and branching/cross-linking. Here we report first example of ambient-temperature ruthenium-catalyzed induced by visible light irradiation. The present can produce various meta- para-linked excellent yields with high molecular weights. remarkable feature our mild platform represented chemoselectivity, leading to that are otherwise inaccessible under conventional at temperatures.

Язык: Английский

Процитировано

4

Radical Addition-Enabled C–C σ-Bond Cleavage/Reconstruction to Access Functional Indanones: Total Synthesis of Carexane L DOI
Cong Shi, Ruihua Liu, Zemin Wang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(15), С. 2913 - 2917

Опубликована: Апрель 3, 2024

C–C σ-bond cleavage and reconstruction is a significant tool for structural modification in synthetic chemistry but it remains formidable challenge to perform on unstrained skeletons. Herein, we describe radical addition-enabled cleavage/reconstruction reaction of allyl ketones access various functional indanones bearing benzylic quaternary center. The utility this method has been showcased by the first total synthesis carexane L, an indanone-based natural product.

Язык: Английский

Процитировано

3

Ruthenium-Catalyzed Remote Trifunctionalization of Non-Activated Alkenes via Cyano Migration and meta-C(sp2)–H Functionalization DOI
Junlei Zhang, Xixi Zhao,

You-Zhi Liao

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 28, 2025

A novel Ru-catalyzed radical-triggered trifunctionalization of hexenenitriles is presented, employing a strategy remote cyano group migration and meta-C(sp2)-H functionalization. Through migration, the alkenyl moiety undergoes difunctionalization to formation benzylic radical intermediate. This intermediate facilitates para-selective C-H bond addition relative C-Ru within Ru(III) complex, ultimately enabling trifunctionalization. methodology provides an efficient route diverse array nitrile-containing compounds with broad functional compatibility.

Язык: Английский

Процитировано

0

Photoinduced Ruthenium-Catalyzed meta-C–H Glycosylation DOI Creative Commons

Julia Pöhlmann,

Binbin Yuan, Purushothaman Rajeshwaran

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 10542 - 10549

Опубликована: Июнь 5, 2025

Язык: Английский

Процитировано

0

A high-efficiency and durable flame retardant for cotton fabrics: Ammonium ethyl acryloylphosphoramidate DOI
Qing Jing,

Yonghua Lu,

Tian Li

и другие.

International Journal of Biological Macromolecules, Год журнала: 2024, Номер 278, С. 134915 - 134915

Опубликована: Авг. 22, 2024

Язык: Английский

Процитировано

3

meta-C–H functionalization of phenylethyl and benzylic alcohol derivatives via Pd/NBE relay catalysis DOI Creative Commons

Hua‐Chen Shen,

Jian-Jun Li,

Peng Wang

и другие.

Chemical Science, Год журнала: 2024, Номер 15(38), С. 15819 - 15824

Опубликована: Янв. 1, 2024

The transition metal-catalyzed meta -C–H functionalization of alcohols and their hydroxylamine derivatives remains underdeveloped.

Язык: Английский

Процитировано

2

Biomimetic Catalytic Remote Desaturation of Aliphatic Alcohols DOI Creative Commons
Kaiming Zuo,

Jing Zhu,

Faral Akhtar

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 23, 2024

Herein we present photoinduced cobaloxime-catalyzed selective remote desaturation of aliphatic alcohols. This transformation, which proceeds efficiently at room temperature, facilitates the synthesis valuable cyclic and acyclic allylic homoallylic alcohols from readily available saturated Remarkably, this method obviates need for external oxidants, noble metal catalysts, phosphine ligands.

Язык: Английский

Процитировано

2

A Novel Approach to α‐Arylacetonitrile Skeletons via para‐Selective Alkylation of Protected Anilines DOI

Zefeng Deng,

Wei‐Tai Fan,

Jian Liu

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(44)

Опубликована: Май 23, 2023

A ruthenium-catalyzed para-selective alkylation of protected anilines to construct α-arylacetonitrile skeletons has been reported. We firstly disclosed the ethyl 2-bromo-2-cyanopropanoate was an effective alkylating reagent in ruthenmuim-catalyzed remote-selective C-H functionalization. wide variety can be directly obtained with moderate good yields. Importantly, products contain both nitrile and ester groups guaranteeing its direct transformation into other useful synthetic units, indicating importance this method.

Язык: Английский

Процитировано

4