Three-component tandem remote C-H functionalization of naphthalenes by ruthenium catalysis: Modular and concise synthesis of multifunctional naphthalenes DOI Creative Commons

Mao‐Gui Huang,

Yue-Liu-Ting Fu,

Jia‐Wei Li

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 12, 2024

A versatile multi-component strategy for synthesizing multi-functional naphthalenes via ruthenium-catalyzed tandem C5–H functionalization from readily available naphthalene, olefin and alkyl bromide compounds is disclosed.

Language: Английский

Carbon monoxide enabling synergistic carbonylation and (hetero)aryl migration DOI
Yuanrui Wang,

Hefei Yang,

Yan Zheng

et al.

Nature Catalysis, Journal Year: 2024, Volume and Issue: 7(10), P. 1065 - 1075

Published: Aug. 6, 2024

Language: Английский

Citations

13
Silylarylation of Alkenes via meta-Selective C–H Activation of Arenes under Ruthenium/Iron Cooperative Catalysis: Mechanistic Insights from Combined Experimental and Computational Studies DOI

Sukanya Neogi,

Sourav Bhunya,

Asim Kumar Ghosh

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 4510 - 4522

Published: March 12, 2024

Organosilicons are privileged skeletons in the domains of pharmaceutical chemistry, organic synthesis, and materials science. Hence, investigating catalytic techniques for synthesis organosilicon compounds has received a great deal emphasis. Carbosilylation alkenes is an efficient technique to introduce diverse molecular architectures containing silicon into chemical space. However, organohalides pseudohalides prerequisites most existing carbosilylation protocols. On other hand, utilization C–H activation been sowing seeds successful development intricate scaffolds. In this regard, synthetic accessibility complexed derivatives by through meta-C–H approach remained intangible. Herein, we present three-component strategy arylsilylation olefins with (het)arenes silanes integrating iron-catalyzed silyl radical generation, coupled intrinsic reactivity alkene, ruthenium-catalyzed functionalization (het)arene, leading targeted cross-coupled carbosilylated product. addition, theoretical investigations state-of-the-art dispersion corrected density functional theory at B3PW91-D3/Def2TZVP/CPCM(PhCF3) shed intriguing insights on selectivity probable mechanistic pathway underexplored cooperative 3d/4d transition metal catalysis, such as formation its addition alkene catalyzed iron, followed meta-selective ruthenium bound arene, furnishing C4 substituted (het)arene functionalized compounds.

Language: Английский

Citations

10
N-Phenylphenothiazine-based Hyper-cross-linked Polymers for Recyclable, Heterogeneous Photocatalysis of Organic Transformations: A Strategy to Access 6-Difluoromethyl-phenanthridines DOI

Shengjie Song,

Wenjian Wang,

Yali He

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 23, 2025

Herein, a N-phenylphenothiazine-based hyper-cross-linked polymer (PTH-HCP) was finely designed and constructed, which serves as metal-free heterogeneous photocatalyst for organic transformations. Characterization experiments have shown that this demonstrates outstanding stability, extensive surface area, exceptional photoelectric response properties. Moreover, PTH-HCP showed good catalytic efficiency recyclability in the photochemically driven difluoromethylation/cyclization reactions. This work provides strategy design construction of photocatalysts offers support their broad prospects synthetic applications.

Language: Английский

Citations

1
Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C−C cleavage and ruthenium-catalysed remote C−H activation DOI Creative Commons
Shan Chen,

Zhimin Xu,

Binbin Yuan

et al.

Nature Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

Language: Английский

Citations

1
Unlocking regioselective meta-alkylation with epoxides and oxetanes via dynamic kinetic catalyst control DOI Creative Commons

Peng‐Bo Bai,

Alastair J. Durie, Gang‐Wei Wang

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Jan. 2, 2024

Abstract Regioselective arene C−H bond alkylation is a powerful tool in synthetic chemistry, yet subject to many challenges. Herein, we report the meta -C−H of aromatics bearing N -directing groups using (hetero)aromatic epoxides as alkylating agents. This method results complete regioselectivity on both well epoxide coupling partners, cleaving exclusively benzylic C−O bond. Oxetanes, which are normally unreactive, also participate reagents under reaction conditions. Our mechanistic studies reveal an unexpected reversible ring opening process undergoing catalyst-controlled regioselection, key for observed high regioselectivities.

Language: Английский

Citations

8
Visible-Light-Mediated Bimetal-Catalyzed meta-Alkylation of Arenes DOI
Pengcheng Cui, Guan‐Wu Wang

Organic Letters, Journal Year: 2024, Volume and Issue: 26(2), P. 427 - 432

Published: Jan. 8, 2024

A mild approach to the visible-light-mediated bimetal-catalyzed meta-alkylation of arenes has been accomplished. The regioselective is realized by a bimetallic ruthenium–palladium system. Ruthenium acts as catalyst for directing effect and photosensitizer, while cocatalyst palladium behaves generation fluoroalkyl radicals. This reaction not only suitable two-component meta-fluoroalkylation but can also be extended three-component reactions achieve bifunctionalization olefins.

Language: Английский

Citations

8
Visible-Light-Mediated Ruthenium-Catalyzed para-Selective Alkylation of Unprotected Anilines DOI
Xinyan Lv,

Yaohang Cheng,

Yingxiao Zong

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(11), P. 7310 - 7321

Published: May 15, 2023

Anilines are important moieties in organic chemistry, pharmaceuticals, and materials science. Although para-selective functionalization of anilides tertiary anilines is well established, unprotected have posed a challenge. Herein, we report visible-light-mediated Ru(II)-catalyzed para-alkylation anilines. The distinct Ru(II)–aniline complex enabled the reaction to proceed with extremely high efficiency (2 h) under mild conditions. good functional group tolerance allowed late-stage even aggregation-induced emission luminogen labeling natural products drugs. A mechanistic investigation suggests that crucial for both triggering controlling para-selectivity.

Language: Английский

Citations

14
Ruthenium-Catalyzed Difunctionalization of Vinyl Cyclopropanes for Double m-C(sp2)–H/C-5(sp3)–H Functionalization DOI

Yu‐Yong Luan,

Jinye Li,

Wei‐Yu Shi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3213 - 3217

Published: April 4, 2024

With in-depth research on 1,2-difunctionalization, remote difunctionalization has garnered widespread attention for achieving multifunctionality. Herein, we report a strategy under mild conditions. This exhibited good substrate suitability and functional group tolerance. In addition, the significance of this method is further evidenced by its successful application in scaling up conducting additional transformations target compounds. Mechanistic studies showed that radical might be involved process.

Language: Английский

Citations

5
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

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 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.

Language: Английский

Citations

4
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

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 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.

Language: Английский

Citations

0