Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation DOI
Kelu Yan, Xiaoyu Wang, Jiangwei Wen

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(43)

Published: Oct. 21, 2022

Abstract The hydroxyl‐directed iridium‐catalyzed peri ‐selective C−H bond activation to synthesize substituted pyrano[2,3,4‐ de ]chromen‐2‐ones and further chalcogenylation under blue light irradiation has been realized efficiently. Most products of polycyclic pyrans corresponding chalcogenated derivatives with various substituents were achieved in good excellent yields. Preliminary mechanistic studies suggest that this transformation may pass through a five‐membered iridacycle intermediate containing an O−Ir σ‐bond photocatalytic free radical process.

Language: Английский

Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes DOI
Xiao Liu, Bingxin Zhou, Kelu Yan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1744 - 1750

Published: Feb. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Language: Английский

Citations

6

Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization DOI

Yicong Ge,

Qiang Yan,

Jiang Nan

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5717 - 5734

Published: Jan. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Language: Английский

Citations

16

Chemical upcycling of poly(bisphenol A carbonate) to vinylene carbonates through organocatalysis DOI Creative Commons
Killian Onida,

Mohamad Fayad,

Sébastien Norsic

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(11), P. 4282 - 4291

Published: Jan. 1, 2023

The chemical upcycling of poly(bisphenol A carbonate) was carried out through organocatalysis using α-hydroxyketones as nucleophiles, leading to valuable vinylene carbonates.

Language: Английский

Citations

11

Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions DOI Open Access

Xiaofan Cui,

Rémi Chauvin, Chao Pi

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3400 - 3412

Published: Sept. 6, 2023

Abstract Recently, vinylene carbonate has been developed as a powerful synthon in transition metal‐catalyzed C−H bond activation/cyclization reactions. This review introduces recent progress the use of reactant, by analyzing and comparing reaction models involving surrogate ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms synthetic applications.

Language: Английский

Citations

11

Transition Metal‐Catalyzed Direct Functionalization of Carbazoles DOI
Vikash Kumar,

S. Sudharsan,

Lusina Mantry

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

Abstract Carbazoles are an important class of nitrogen‐containing heterocycles found in diverse natural products, bioactive molecules, and functional materials. Their broader applications have driven extensive research into their synthesis functionalization. Among various approaches, transition metal‐catalyzed C−H activation has emerged as a powerful tool for direct functionalization, offering regioselectivity, efficiency, sustainability. This review comprehensively summarizes advancements functionalization carbazoles. Various catalytic systems employing palladium, ruthenium, rhodium, nickel, cobalt, copper, iron enabled alkylation, alkenylation, acylation, arylation, alkynylation, heteroatom incorporation These methodologies late‐stage diversification opened avenues accessing structurally complex carbazole derivatives with tailored properties. The aims to provide comprehensive guide researchers exploring via activation, highlighting key mechanistic insights, scope, emerging trends this field.

Language: Английский

Citations

0

Cobalt(III)-Catalyzed Directed C-7 Selective C–H Alkynylation of Indolines with Bromoalkynes DOI
Ruihan Niu, Jing Zhang, Ruyuan Zhao

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(29), P. 5411 - 5415

Published: July 17, 2023

A cobalt(III)-catalyzed directed C-7 alkynylation of indolines with easily accessible bromoalkynes has been developed. The reaction a broad substrate scope excellent yields and represents powerful route to the synthesis 7-alkynyl-substituted indolines. In addition, can be extended coupling N-aryl 7-azaindoles, highlighting synthetic practicability strategy.

Language: Английский

Citations

10

Transition-Metal-Catalyzed Directed C8–H Carbon–Carbon Bond Formation in Quinolines and 1,2,3,4-Tetrahydroquinolines DOI
Tharmalingam Punniyamurthy, Shubhajit Basak, Tripti Paul

et al.

Synthesis, Journal Year: 2023, Volume and Issue: 55(21), P. 3454 - 3469

Published: March 20, 2023

Abstract C8-Substituted quinoline (QN) and 1,2,3,4-tetrahydroquinoline (THQ) scaffolds are featured in numerous bioactive compounds natural products. Appreciable efforts have been made towards the development of elegant techniques to functionalize C8–H bond QNs THQs. The transition-metal-catalyzed chelation-assisted C–H activation strategy has emerged as an effective synthetic tool among existing methods. This review focuses on recent advances directed carbon–carbon forming reactions for functionalization THQs (till February 2023). discussion categorized based type reaction. 1 Introduction 2 Acylation 3 Alkylation 4 Alkenylation 5 Alkynylation 6 Allylation 7 Annulation 8 Arylation 9 Conclusion Outlook

Language: Английский

Citations

7

Experimental and Computational Studies on RuII‐Catalyzed C7‐Allylation of Indolines with Allyl Bromide DOI
Shiv Shankar Gupta, Shivangi Gupta,

XXXXXXX Manisha

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(50)

Published: June 26, 2023

The selective C7-allylation of indolines with allyl bromide under ruthenium catalysis has been revealed here. Under established reaction conditions, various indolines, including drug compounds, was accomplished good selectivity and yields. Based on combined experimental density functional theory (DFT) studies, the olefin insertion route energetically favorable among four possible pathways. Experimental DFT studies further that C-H activation is a reversible rate-limiting step.

Language: Английский

Citations

7

Rhodium(III‐Catalyzed C8‐Selective C−H Alkenylation and Alkylation of 1, 2, 3, 4‐Tetrahydroquinolines with Styrenes and Allylic Alcohols DOI
Ji Yang, Changjun Chen, Haoqiang Zhao

et al.

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(7), P. 1027 - 1035

Published: March 16, 2023

Abstract Rh(III)‐catalyzed chelation‐assisted C8‐selective C−H alkenylation and alkylation of 1,2,3,4‐tretrahydroquinolines with styrenes allylic alcohols have been realized. The cationic Rh(III) catalytic system in combination a amount copper acetate uses oxygen as the terminal oxidant catalyzes stereoselective C8‐alkenylation 1,2,3,4‐tetrahydroquinolines to give corresponding products 56–93% yields wide substrate scope broad functional group compatibility. reaction can be scaled up. Moreover, this protocol extended C8‐alkylation alcohols, providing access various 8‐(3‐oxoalkyl)‐1,2,3,4‐tetrahydroquinolines 77–90% yields. selection N‐directing is essential for catalysis, readily installable removable N‐(2‐pyrimidyl) proves optimal choice. Preliminary mechanistic studies are performed gain insights into mechanism. magnified image

Language: Английский

Citations

5

Rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinones with vinylene carbonate DOI
Jiang Nan, Liang Lu

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(98), P. 14559 - 14562

Published: Jan. 1, 2023

A novel organic transformation involving rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinone with vinylene carbonate is reported, and the promising reagent presents a distinct chemical reactivity as vinyl-oxygen cyclic synthon.

Language: Английский

Citations

4