Cobalt-Catalyzed Reductive Cross-Coupling To Construct Csp3–Csp3 Bonds via Csp3–S and Csp3–X Bonds Activation DOI
Mengyu Gao, Corinne Gosmini

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7689 - 7693

Published: Oct. 18, 2023

A cross-electrophilic coupling of benzyl sulfonium salts with alkyl halides forming Csp3–Csp3 bonds is described by using a Co-based catalytic system. The activation the stable Csp3–S bond under mild reaction conditions leads to various functionalized derivatives. Preliminary mechanistic studies suggest involvement radicals formed from both and sulfoniums through single electron transfer.

Language: Английский

Nickel-Catalyzed Direct Cross-Coupling of Aryl Sulfonium Salt with Aryl Bromide DOI
Nana Ma,

Jing‐Ao Ren,

Xiang Liu

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(10), P. 1953 - 1957

Published: March 4, 2022

The direct cross-couplings of aryl sulfonium salts with halides could be achieved by using nickel as a reaction catalyst. reactions proceeded efficiently via C-S bond activation in the presence magnesium turnings and lithium chloride THF at ambient temperature to afford corresponding biaryls moderate good yields, potentially serving an attractive alternative conventional cross-coupling employing preprepared organometallic reagents.

Language: Английский

Citations

44
Comproportionation and disproportionation in nickel and copper complexes DOI
Craig S. Day, Rubén Martı́n

Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(19), P. 6601 - 6616

Published: Jan. 1, 2023

This review covers factors that contribute to comproportionation and disproportionation reactions in transition metal complexes provide insight into the importance of these electron transfer events Ni- Cu-catalyzed transformations.

Language: Английский

Citations

39
Copper‐Catalyzed C4‐selective Carboxylation of Pyridines with CO2 via Pyridylphosphonium Salts DOI

Shibiao Tang,

Zezhao Liu,

Jiakai Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(13)

Published: Feb. 3, 2024

Abstract Pyridine motifs are widespread pharmacophores in many drugs. Installing various substituents through pyridine C−H bond functionalization is significant for new drug design and discovery. Developments of late‐stage reactions enrich the strategies selective pyridines. However, carboxylation pyridines a long‐standing challenge, especially selectively with CO 2 on motifs. Herein, we describe practical method C4−H via one‐pot phosphination copper‐catalyzed resulted phosphonium salts . The reaction conducted under mild conditions compatible multiple active groups several drugs, providing diverse valuable isonicotinic acid compounds, demonstrating application potential this strategy.

Language: Английский

Citations

11
Electrocatalytic Formal C(sp2)−H Alkylations via Nickel‐Catalyzed Cross‐Electrophile Coupling with Versatile Arylsulfonium Salts DOI Creative Commons
Takuya Michiyuki, Simon L. Homölle, Neeraj Kumar Pandit

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(29)

Published: May 2, 2024

Producing sp

Language: Английский

Citations

11
Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions DOI Creative Commons

Xuan-Bo Hu,

Qian-Qian Fu,

Xueying Huang

et al.

Molecules, Journal Year: 2024, Volume and Issue: 29(4), P. 831 - 831

Published: Feb. 13, 2024

Hydroxylation of aryl sulfonium salts could be realized by utilizing acetohydroxamic acid and oxime as hydroxylative agents in the presence cesium carbonate a base, leading to variety structurally diverse hydroxylated arenes 47–95% yields. In addition, reaction exhibited broad functionality tolerance, range important functional groups (e.g., cyano, nitro, sulfonyl, formyl, keto, ester) well amenable mild conditions.

Language: Английский

Citations

10
Efficient palladium-catalyzed electrocarboxylation enables late-stage carbon isotope labelling DOI Creative Commons
Gabriel M. F. Batista, Ruth Ebenbauer, Craig S. Day

et al.

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

Published: March 22, 2024

Abstract Carbon isotope labelling of bioactive molecules is essential for accessing the pharmacokinetic and pharmacodynamic properties new drug entities. Aryl carboxylic acids represent an important class structural motifs ubiquitous in pharmaceutically active are ideal targets installation a radioactive tag employing isotopically labelled CO 2 . However, direct incorporation via reported catalytic reductive carboxylation (CRC) aryl electrophiles relies on excess , which incompatible with carbon-14 incorporation. Furthermore, application some CRC reactions late-stage limited because low tolerance molecular complexity by catalysts. Herein, we report development practical affordable Pd-catalysed electrocarboxylation setup. This approach enables use near-stoichiometric 14 generated from primary source Ba 3 facilitating single-step pharmaceuticals representative precursors. The proposed isotope-labelling protocol holds significant promise immediate impact programmes.

Language: Английский

Citations

10
Closing the Anthropogenic Chemical Carbon Cycle toward a Sustainable Future via CO2 Valorization DOI
Jiawei Zhang, Christopher D. Sewell,

Hongwen Huang

et al.

Advanced Energy Materials, Journal Year: 2021, Volume and Issue: 11(47)

Published: Nov. 5, 2021

Abstract Concerns over the massive increase in CO 2 emissions induced by overconsumption of fossil fuels have driven rapid development valorization techniques. Carbon capture and utilization (CCU) technology, which emerged as a promising strategy to relieve increasing environmental concerns create more carbon feedstocks simultaneously, hold great promise close anthropogenic chemical cycle. Herein, recent breakthroughs related two predominant techniques involved returning into useful state, namely conversion are systematically overviewed. Initially, principles, advances, well future challenges state‐of‐the‐art absorbents/adsorbents membrane separation technology summarized. Furthermore, innovative catalysts technologies (including thermo‐driven hydrogenation, photo‐and electrochemical reduction, enzymatic conversion) discussed, emphasis is focused on catalytic performance, design economic efficiency. Finally, perspective regarding research opportunities toward CCU provided. This review aims stimulate innovation accelerate interdisciplinary integrations via discussion fundamental mechanisms, breakthroughs, current associated difficulties directions.

Language: Английский

Citations

51
Enantioselective CO2 Fixation Via a Heck‐Coupling/Carboxylation Cascade Catalyzed by Nickel DOI

Alessandro Cerveri,

Riccardo Giovanelli,

Davide Sella

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(28), P. 7657 - 7662

Published: April 8, 2021

Abstract A novel asymmetric nickel‐based procedure has been developed in which CO 2 fixation is achieved as a second step of truncated Heck coupling. For this, new chiral ligand prepared and shown to achieve enantiomeric excesses up 99 %. The overall process efficiently furnishes 2,3‐dihydrobenzofuran‐3‐ylacetic acids, an important class bioactive products, from easy prepare starting materials. combined experimental computational effort revealed the key steps catalytic cycle suggested unexpected participation Ni(I) species coupling event.

Language: Английский

Citations

45
Nickel-Catalyzed Cross-Electrophile Coupling between C(sp2)–F and C(sp2)–Cl Bonds by the Reaction of ortho-Fluoro-Aromatic Amides with Aryl Chlorides DOI

Itsuki Nohira,

Naoto Chatani

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(8), P. 4644 - 4649

Published: April 2, 2021

Ni-catalyzed cross-electrophile coupling between C(sp2)–F bonds in ortho-fluoro-substituted aromatic amides and C(sp2)–Cl aryl chlorides the presence of Zn as a reductant LiOtBu base, LiCl ZnCl2 additives is reported. The reaction displayed excellent functional group tolerance broad substrate scope. was also applicable to C(sp2)–O an tosylate triflate derivative.

Language: Английский

Citations

45
Visible-light-initiated catalyst-free trifluoromethylselenolation of arylsulfonium salts with [Me4N][SeCF3] DOI
Zeyu Tian, Cheng‐Pan Zhang

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(8), P. 2220 - 2227

Published: Jan. 1, 2022

Catalyst-free visible-light irradiation has leveraged the big redox potential gaps between arylsulfonium salts and [Me 4 N][SeCF 3 ], which combined with sulfenylation processes offers convenient selective C–H trifluoromethylselenolation.

Language: Английский

Citations

34