The Progress of Reductive Coupling Reaction by Iron Catalysis DOI
Jian‐Qiang Zhao, Zhangpei Chen

The Chemical Record, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 17, 2024

Abstract The transition metal catalyzed coupling reaction has revolutionized the strategies for forging carbon‐carbon bonds. In contrast to traditional cross‐coupling methods using pre‐prepared nucleophilic organometallic reagents, reductive reactions C−C bonds formation provide some advantages. Because both partners are reduced in final products a stoichiometric amount of reductant, this approach not only avoids need use sensitive species, but also provides an orthogonal and complementary access classical reaction. Notably, feature readily available fragments, promote good step economy, exhibit high functional group tolerance unique chemoselectivity, which have propelled their increasingly popular organic synthesis. recent years, due low price, minimal toxicity, environmentally benign character, iron‐catalyzed garnered significant attention from synthetic chemists pharmacologists, especially coupling. This review aims insightful overview advances reactions, illustrate possible mechanisms.

Language: Английский

Nucleophilic Substitution at Unactivated Arene C–H: Copper-Catalyzed anti-Selective Silylative Cyclization of Substituted Benzylacetylenes DOI

Hirokazu Moniwa,

Ryo Shintani

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

Published: Feb. 13, 2025

A new mode of carbon-carbon bond formation via electrophilic activation a C-H has been developed in the context copper-catalyzed anti-selective silylative cyclization benzylacetylenes with silylboronates for synthesis 2-silyl-1H-indenes. The reaction proceeds high regioselectivity various substituted benzylacetylenes, and resulting products could be further functionalized. arene that undergoes acts as an electrophile release hydride under redox neutral conditions, mechanism was probed by deuterium-labeling experiments density functional theory calculations.

Language: Английский

Citations

1
Rhenium-Catalyzed C(sp2)–H Silylalkenylation of Arenes: An Anti-Markovnikov Linchpin Strategy DOI
Suman Bhowmick,

Annapurna Awasthi,

Khushboo Tiwari

et al.

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

Published: Feb. 28, 2025

Re-catalyzed highly regio- and stereoselective o-C(sp2)–H silylalkenylation of arenes is reported using a directing group approach under ligand-, additive-, base-free conditions. A series imine groups (DGs) have been exploited on aromatic aldehydes to overcome de novo synthesis. This unique protocol allows us access o-C–H activation various heterocyclic moieties, including N-aryl 2-pyridones arylpyridines. Sequential difunctionalization experiments performed. mechanistic carried out gain insight.

Language: Английский

Citations

1
Dual Electric Fields in Ni-CdS@Ni(OH)2 Heterojunction: A Synergistic Spatial Charge Separation Approach for Enhanced Coupled CO2 Photoreduction and Selective Toluene Oxidation DOI Creative Commons
Khakemin Khan, Ahmed Mahmoud Idris, Haseebul Hassan

et al.

Advanced Powder Materials, Journal Year: 2025, Volume and Issue: unknown, P. 100284 - 100284

Published: March 1, 2025

Language: Английский

Citations

1
Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones DOI

Mingshuai Zhang,

Longkun Chen,

Zhuoyuan Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5660 - 5666

Published: Jan. 1, 2023

Highly functionalized 3a,7a-dihydroxy hexahydro-4 H -indol-4-ones were efficiently synthesized via a Ru( iii )-catalyzed alkenyl C(sp 2 )–H bond functionalization/[3 + 2] annulation reaction between readily available enaminones and iodonium ylides.

Language: Английский

Citations

20
Nickel-Catalyzed Functionalization Reactions Involving C–H Bond Activation via an Amidate-Promoted Strategy and Its Extension to the Activation of C–F, C–O, C–S, and C–CN Bonds DOI
Naoto Chatani

Accounts of Chemical Research, Journal Year: 2023, Volume and Issue: 56(21), P. 3053 - 3064

Published: Oct. 11, 2023

ConspectusThe development of functionalization reactions involving the activation C-H bonds has evolved extensively due to atom and step economy associated with such reactions. Among these reactions, chelation assistance been shown provide a powerful solution serious issues reactivity regioselectivity faced in bonds. The vast majority reported thus far involved use precious metals. Kleiman Dubeck cyclonickelation azobenzene NiCp2 which an azo group directs Ni center activate ortho bond close proximity. Although this stoichiometric reaction was discovered earlier than that for other transition-metal complexes, its as catalytic delayed. No general systems were available Ni-catalyzed long time. This Account details our group's Ni(0)- Ni(II)-catalyzed chelation-assisted It also highlights how new strategy can be extended unreactive bonds.In early 2010s, we found Ni(0)-catalyzed aromatic amides contain 2-pyridinylmethylamine moiety directing alkynes results C-H/N-H oxidative annulation give isoquinolinones. In addition, combination Ni(II) catalyst 8-aminoquinoline superior developing wide variety various electrophiles. proposed include formation unstable Ni(IV) and/or Ni(III) species; generation high-valence species rare at time, but since then, many papers dealing DFT organometallic studies have appeared literature attempts understand mechanism. Based on in-depth considerations mechanism respect why N,N-bidentate is required, realized N-Ni by addition N-H Ni(0) or ligand exchange between key step. We concluded precoordination N(sp2) positions proximity permits bond. working hypothesis, carried out using KOtBu base do not specific desired isoquinolinone, amidate anion acts actual group. Remarkably, applicable C-F, C-O, C-S, C-CN.

Language: Английский

Citations

17
Regiodivergent sp3 C–H Functionalization via Ni-Catalyzed Chain-Walking Reactions DOI Creative Commons
Jesus Rodrigalvarez, Franz‐Lucas Haut, Rubén Martı́n

et al.

JACS Au, Journal Year: 2023, Volume and Issue: 3(12), P. 3270 - 3282

Published: Nov. 28, 2023

The catalytic translocation of a metal catalyst along saturated hydrocarbon side chain constitutes powerful strategy for enabling bond-forming reactions at remote, yet previously unfunctionalized, sp3 C–H sites. In recent years, Ni-catalyzed chain-walking have offered counterintuitive strategies forging architectures that would be difficult to accomplish otherwise. Although these evolved into mature tools advanced organic synthesis, it was only recently chemists showed the ability control motion which "walks" throughout alkyl chain. Specialized ligand backbones, additives and judicious choice noninnocent functional groups on allowed design "a la carte" protocols enable regiodivergent scenarios different sites with distinct topological surface areas. Given inherent interest in increasing fraction hybridized carbons medicinal chemistry, might expedite access target leads drug discovery campaigns.

Language: Английский

Citations

17
Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones DOI
Yuanshuang Xu,

Yujing Xiao,

Xinying Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 786 - 791

Published: Jan. 22, 2024

Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones. This protocol forms C–C and C–O bonds in one pot which diazonaphthalen-2(1H)-ones serve as bifunctional reagents, providing both alkyl aryloxy sources. To the best our knowledge, this first example title compounds by using substrates. Notably, method features operational simplicity, good functional group tolerance, high efficiency, atom economy.

Language: Английский

Citations

8
Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis DOI

Aman Hasil,

Rui Chang,

Juntao Ye

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(3), P. 728 - 728

Published: Jan. 1, 2024

Language: Английский

Citations

8
Synthesis of Heptacyclic Compounds through C–H Bond Activation-Initiated Cascade Reactions DOI
Xing He,

Kangli Liu,

Shengnan Yan

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(35), P. 7425 - 7430

Published: Aug. 22, 2024

Presented herein is an atom- and step-economical method enabling the precise assembly of a heptacyclic scaffold containing both azocine indoline units through cascade reactions indolin-1-yl(aryl)methanimines with diazo indanediones. The formation products involves C–H bond activation double carbene insertion followed by intramolecular condensation, retro-[2 + 2] cycloaddition, recyclization. This reaction not only provided concise straightforward strategy for synthesis otherwise difficult to obtain compounds from readily available substrates but also disclosed unprecedented mode derivatives compounds. In general, this novel synthetic protocol has advantages, such as easily obtainable substrates, structurally sophisticated products, procedure, good compatibility diverse functional groups, ready scalability. Moreover, thus obtained showed decent antiproliferative activity against three human cancer cell lines.

Language: Английский

Citations

8
Recent advances in hydrogen atom transfer induced C(sp3)–H functionalizations initiated by radical addition to alkynes DOI
Yulu Zhou, Zhenyu Gu,

Yuwei Hong

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(4), P. 1232 - 1250

Published: Dec. 28, 2023

Recent advances in HAT-induced C(sp 3 )–H functionalizations triggered by radical addition to alkynes, including 5- exo-trig , endo-trig 4- and 6- cyclization cascades, intermolecular functionalizations, are summarized.

Language: Английский

Citations

15