Ni‐Catalyzed C(sp 2 )H Bond Functionalization: Trifluoromethylation, Thiolation, and Selenylation DOI
Nidhi Garg,

Bholanath Garai,

Basker Sundararaju

et al.

Handbook of CH‐Functionalization, Journal Year: 2022, Volume and Issue: unknown, P. 1 - 42

Published: Oct. 1, 2022

Abstract This article is intended to provide a concise review of the seminal work on nickel‐catalyzed direct “sp 2 ” CH bond functionalizations, with particular focus trifluoromethylation, thiolation, and selenylation. The current mechanistic hypotheses were described for deeper understanding that should aid in future design various other efficient transformations. We anticipate continued research this area help extend applications late‐stage functionalization bioactive molecules.

Language: 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, Journal Year: 2022, Volume and Issue: 122(21), P. 16110 - 16293

Published: Sept. 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.

Language: Английский

Citations

201

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

et al.

Green Synthesis and Catalysis, Journal Year: 2022, Volume and Issue: 4(3), P. 226 - 230

Published: April 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.

Language: Английский

Citations

17

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

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(31), P. 6072 - 6177

Published: Jan. 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.

Language: Английский

Citations

15

Copper(II)-catalyzed, Site Selective C(sp2)–H Amination using 8-Aminoimidazo[1,2-a]pyridine (AIP) as Directing group DOI

Arun Kumar Hajra,

Prasanjit Ghosh,

Chandrayee Roy

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6617 - 6630

Published: Jan. 1, 2024

A ubiquitous copper( ii )-catalyzed regioselective ortho C(sp 2 )–H amination of arenes/heteroarenes has been revealed with the assistance 8-AIP (8-aminoimidazo[1,2- a ]pyridine) as an efficacious 6,5-fused bicyclic removable chelating auxiliary.

Language: Английский

Citations

2

Site-specific C–H chalcogenation of quinoxalin-2(1H)-ones enabled by Selectfluor reagent DOI
Jinwei Yuan, Yang Zhang,

Guang-Chao Huang

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(24), P. 6937 - 6949

Published: Jan. 1, 2021

A site-specific C6–H chalcogenation of quinoxalin-2(1 H )-ones with various diselenides and dithiols is presented by employing Selectfluor reagent as an oxidant.

Language: Английский

Citations

16

Cu(II)-Catalyzed C–N, C–O, C–Cl, C–S, and C–Se Bond Formation via C(sp2)–H Activation Using 7-Azaindole as an Intrinsic Directing Group DOI
Mohit Kumar,

Raziullah,

Gulraız Ahmad

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(21), P. 15185 - 15202

Published: Oct. 26, 2021

A general protocol has been developed for the construction of carbon-heteroatom (C-N, C-Cl, C-O, C-S, and C-Se) bonds using bench stable, earth-abundant, environmentally benign copper catalyst. Only oxygen is sufficient to regenerate Control experiments suggested that proto-demetalation step reversible. Depending on coupling partner, reaction follows either disproportionation or radical pathways complete catalytic cycle. The synthetic utility demonstrated via various functional group transformations.

Language: Английский

Citations

13

Research Progress in C—S Coupling Reactions of Aryl Halides DOI Open Access

Sining Qin

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(11), P. 3761 - 3761

Published: Jan. 1, 2023

Sulfur-containing compounds are widely found in natural products, pharmaceuticals, pesticides, and materials, possessing a variety of biological activities or unique functions.C-S coupling reaction is an important method for the synthesis sulfur-containing one hot spots field organic synthesis.With in-depth development catalysts continuous expansion partners, large number C-S reactions have emerged recent years, which greatly facilitate compounds.Aryl halides main kind substrates compounds.C-S aryl partners can efficiently afford compounds, such as thiophenols, thioethers, disulfides sulfones different well-designed systems.In this review, with reviewed according to types (palladium, copper, nickel, others).The mechanisms representative briefly described compared.In addition, brief analysis current situations limitations given, prospect future put forward.

Language: Английский

Citations

5

Rhodium-catalyzed selenylation and sulfenylation of quinoxalinones ‘on water’ DOI Creative Commons
Ram Sunil Kumar Lalji,

Prince,

Mohit Gupta

et al.

RSC Advances, Journal Year: 2023, Volume and Issue: 13(9), P. 6191 - 6198

Published: Jan. 1, 2023

A rhodium-catalysed, regioselective synthetic methodology for selenylation and sulfenylation of 3-phenyl quinoxolinones has been developed through N-directed C-H activation in the presence silver triflimide, carbonate using dichalcogenides 'on water'. The proven to be efficient, green. Using this method, a range selenylations sulfenylations substrates carried out good excellent yields. Further, late-stage functionalisation produced potential anti-tumour, anti-fungal anti-bacterial agents making these compounds drug candidates.

Language: Английский

Citations

4

Ru(II)‐Catalyzed ortho C—H Allylation of N‐Aryl‐7‐azaindoles with 2‐Methylidene Cyclic Carbonate DOI
Jing Zhang,

Quanjian Luo,

Han‐Chi Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(9), P. 985 - 989

Published: Dec. 26, 2023

Comprehensive Summary A Ru(II)‐catalyzed ortho allylation reaction of N ‐aryl‐7‐azaindole with readily available 2‐methylidene cyclic carbonate has been developed. This is an effective pathway for synthesizing 7‐azaindole derivatives a wide scope substrates and high yields. In addition, the method can be extended to other heterocyclic compounds several carbonates, highlighting practicality this strategy synthesis.

Language: Английский

Citations

4

Copper‐Promoted Oxidative Amide‐Assisted Radical Selenylation of Anilides and N‐Arylsulfonamides with Diselenides DOI
Lou Shi,

Penghui Xu,

Yingchun Ma

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(5)

Published: March 21, 2024

Abstract A direct selenylation of N ‐arylsulfonamides and anilides using environmentally friendly readily available copper promoted assisted by amide is presented. This method provided convenient access for various reactions, demonstrating a wide range substrates strong tolerance to functional groups. According the selection reaction substrates, products can be isolated obtain regioselectivity ortho ‐, para or unprecedented , ‐diselenylation products. Such transformation was elucidated proposed copper‐promoted amide‐assisted radical mechanism.

Language: Английский

Citations

1