Research Progress on the Reaction of Carbon Dioxide with Hydrazones and Their Derivatives DOI Creative Commons

Hongxia Sun,

Shao-Xuan Gong,

Hongyang Zhang

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(9), P. 1987 - 1987

Published: April 29, 2025

CO2, an abundant and renewable C1 source, presents significant potential for applications in organic synthesis. Hydrazones, recognized their distinctive properties, exhibit high versatility synthetic chemistry, facilitating numerous chemical transformations. Given crucial roles synthesis, the combination of CO2 with hydrazones has garnered increasing research interest. This review provides a comprehensive summary recent progress reactions involving or derivatives. These include coupling amines N-tosylhydrazones umpolung-mediated carboxylation hydrazones/N-tosylhydrazones cyclization lactamization incorporating CO2. transformations utilize diverse reactivity derivatives to capture convert generating valuable compounds both academic practical relevance. Additionally, examines mechanisms underlying these reactions, offering critical insights advancing this area.

Language: Английский

Organo-mediator enabled electrochemical transformations DOI
Wei-Mei Zeng, Yanwei Wang,

Chunhui Peng

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review highlights organo-mediators that enable electrochemical reactions via outer-sphere electron transfer (ET), offering advantages such as availability, tunability, and simplified post-processing compared to direct electrolysis.

Language: Английский

Citations

1
Visible-Light Photoredox-Catalyzed Direct Carboxylation of Tertiary C(sp3)–H Bonds with CO2: Facile Synthesis of All-Carbon Quaternary Carboxylic Acids DOI
Yi Liu,

Guan-Hua Xue,

Zhen He

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 7, 2024

Direct carboxylation of C–H bonds with CO2 represents an attractive strategy to synthesize valuable carboxylic acids high atom, step, and redox economy. Although great progress has been achieved in this field, catalytic tertiary C(sp3)–H still remains challenging due their inherent inertness significant steric hindrance. Herein, we report a direct benzylic via visible-light photoredox catalysis. Various all-carbon quaternary acids, which are importance medicinal chemistry, successfully obtained yields. This is characterized by good functional group tolerance, broad substrate scope, mild operational conditions. Furthermore, our methodology enables the efficient rapid synthesis key drug or bioactive molecules, such as carbetapentane, caramiphen, PRE-084 (σ1 receptor agonist), facilitates various functionalizations C(sp2)–H using directing ability target thus highlighting its practical applications. Mechanistic studies indicate that carbanion, serves intermediate react CO2, catalytically generated single electron reduction radical through consecutive photoinduced transfer process.

Language: Английский

Citations

5
Electroreductive Cross-Coupling Reactions: Carboxylation, Deuteration, and Alkylation DOI
Pengfei Li, Yanwei Wang, Hanying Zhao

et al.

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 13, 2024

ConspectusElectrochemistry has been used as a tool to drive chemical reactions for more than two centuries. With the help of an electrode and power source, chemists are provided with system whose potential can be precisely dialed in. The theoretically infinite redox range renders electrochemistry capable oxidizing or reducing some most tenacious compounds. Indeed, electroreduction offers alternative generating highly active intermediates from electrophiles (e.g., halides, alkenes, etc.) in organic synthesis, which untouchable traditional reduction methods. Meanwhile, reductive coupling extensively utilized both industrial academic settings due their ability swiftly, accurately, effectively construct C–C C–X bonds, present innovative approaches synthesizing complex molecules. Nonetheless, its application is constrained by several inherent limitations: (a) requirement stoichiometric quantities agents, (b) scarce activation strategies inert substrates high potentials, (c) incomplete mechanistic elucidation, (d) challenges isolation intermediates. merging represents attractive approach address above limitations synthesis seen increasing use synthetic community over past few years.Since 2020, our group dedicated developing electroreductive cross-coupling using readily available small molecules, such arenes, CO2, D2O, value-added products. Electroreductive chemistry versatile powerful capacity precise selectivity control, allowed us develop three electrochemical modes lab: (1) An economically advantageous direct (EDR) strategy that emphasizes efficiency, achieves atom utilization, minimizes unnecessary atomic waste. (2) A class organo-mediated (EOMR) methods controlling reaction pathways. This allows modulation processes enhance efficiency selectivity. (3) metal-catalyzed (EMCR) method enables selective functionalization specific bonds functional groups under mild conditions, thereby occurrence side reactions. We commenced studies establishing organic-mediator-promoted carboxylation aryl alkyl halides. was then employed arylcarboxylation simple styrenes halides manner. electrolysis arenes epoxides CO2 carboxyl source achieved. Moreover, through adjustment we successfully accomplished deuteration olefins, unactivated enabling efficient formation D-labeled Finally, building on previous understanding developed series alkylation enable C(sp3)–C(sp3)

Language: Английский

Citations

4
Transition Metal‐Free Direct Electrochemical Carboxylation of Organic Halides Using a Sacrificial Magnesium Anode: Straightforward Synthesis of Carboxylic Acids DOI Creative Commons

Iryna Lesko,

Stéphane Sengmany,

Raphaël Beltran

et al.

ChemistryOpen, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 28, 2025

Abstract The direct electrochemical carboxylation of aryl, benzyl and alkyl halides by CO 2 is described using a magnesium anode nickel foam cathode in an undivided cell. process employs sacrificial does not require the additional use transition metal catalyst or demanding conditions, as reactions are carried out under galvanostatic mode, at −10 °C with commercial DMF. Under these operationally simple important range carboxylic acids affordable. Mechanistic investigation account for situ generation carbanionic species that organomagnesium halide.

Language: Английский

Citations

0
Anodic reactions matter for cathodic electrocarboxylation with CO2 DOI
Jialu Li, Jie Xiong, Minghao Sun

et al.

Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101263 - 101263

Published: Feb. 1, 2025

Language: Английский

Citations

0
Metallaphotoredox-catalyzed alkynylcarboxylation of alkenes with CO2 and alkynes for expedient access to β-alkynyl acids DOI Creative Commons

Jincheng Xu,

Jun‐Ping Yue, Min Pan

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 21, 2025

Carboxylation with CO2 offers an attractive and sustainable access to valuable carboxylic acids. Among these methods, direct C−H carboxylation of terminal alkynes has attracted much attention for one-carbon homologation alkynes, enabling rapid synthesis propiolic In contrast, the multi-carbons construct important non-conjugated alkynyl-containing acids not been reported. Herein, we present alkynylcarboxylation alkenes via photoredox copper dual catalysis. This protocol provides a practical method form alkynyl from readily available CO2. Additionally, this approach also features mild (room temperature, 1 atm CO2) redox-neutral conditions, high atom step economy, good functional group tolerance, selectivities. Moreover, diverse transformations β-alkynyl acid products bioactive molecule (GPR40/FFA1 agonist) further illustrate synthetic utility methodology. The report multi-carbon is rare. authors catalysis, affording

Language: Английский

Citations

0
CO2 Fixation into Useful Aromatic Carboxylic Acids via C (sp2)–X Bonds Functionalization DOI
Youwen Chen, Mingqiang Chen, Xinyu Li

et al.

Topics in Current Chemistry, Journal Year: 2025, Volume and Issue: 383(1)

Published: March 3, 2025

Language: Английский

Citations

0
Advances in methanol synthesis via MOF-based catalysts: A comprehensive review and critical analysis DOI

Ali Khatib Juma,

Zulkifli Merican Aljunid Merican, Abdurrashid Haruna

et al.

Inorganic Chemistry Communications, Journal Year: 2025, Volume and Issue: unknown, P. 114266 - 114266

Published: March 1, 2025

Language: Английский

Citations

0
A general electrochemical CO2 fixation to aromatic carboxylic acids via the CO2·− intermediate using a non-transition metal electrode DOI

Baijing Wu,

Xiaoxue Luo,

Hongliang Fan

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 28, 2025

Language: Английский

Citations

0
Transforming Highly Oxidized and Reduced Carbon Feedstocks: Strategies for Catalytic CO2 and CH4 Valorization DOI Creative Commons
Nilay Hazari, Hannah S. Shafaat, Jenny Y. Yang

et al.

Accounts of Chemical Research, Journal Year: 2024, Volume and Issue: 57(24), P. 3451 - 3453

Published: Dec. 17, 2024

Language: Английский

Citations

3