Substrate-Controlled Divergent Reductive Cyclization of 2-Arylanilines Using CO2 as a Switching Reagent DOI
Qiang Yan, Jiang Nan,

Rui Cao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 27(1), P. 510 - 516

Published: Dec. 30, 2024

Capturing CO2 is highly valued in the field of organic synthesis, especially underdeveloped dual-CO2 conversion. In this study, we detail a novel reductive cyclization 2-indolylanilines with dual as difunctional reagent presence PMHS [poly(methylhydrosiloxane)], delivering methyl-substituted quinoxalines. Furthermore, another chemoselective 2-pyrrolylanilines also realized by converting mono-CO2. Mechanistic investigations shed light upon fact that substrate-controlled divergence mainly depends on formation N-diacylative intermediates.

Language: Английский

Cu-Catalyzed Diastereo- and Enantioselective Synthesis of Borylated Cyclopropanes with Three Contiguous Stereocenters DOI
Chao Gao, Kai Tang, Xi Yang

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 17, 2025

Direct synthesis of enantioenriched scaffolds with multiple adjacent stereocenters remains an important yet challenging task. Herein, we describe a highly diastereo- and enantioselective Cu-catalyzed alkylboration cyclopropenes, less reactive alkyl iodides as electrophiles, for the efficient tetra-substituted borylated cyclopropanes bearing three consecutive stereocenters. This protocol features mild conditions, broad substrate scope, good functional group tolerance, affording array chiral in to high yields excellent enantioselectivities. Detailed mechanistic experiments kinetic studies were conducted elucidate reaction pathway rate-determining step reaction. DFT calculations revealed that π···π stacking interaction between phenyl groups on phosphorus ligand, along smaller distortion CuL-Bpin part, contributed The synthetic utility was showcased by facile some valuable centers.

Language: Английский

Citations

5

Atropisomeric Carboxylic Acids Synthesis via Nickel‐Catalyzed Enantioconvergent Carboxylation of Aza‐Biaryl Triflates with CO2 DOI
Xiao‐Wang Chen, Chao Li, Yong‐Yuan Gui

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(22)

Published: March 26, 2024

Abstract Upgrading CO 2 to value‐added chiral molecules via catalytic asymmetric C−C bond formation is a highly important yet challenging task. Although great progress on the of centrally carboxylic acids has been achieved, construction axially with never reported date. Herein, we report first synthesis , which enabled by nickel‐catalyzed dynamic kinetic reductive carboxylation racemic aza‐biaryl triflates. A variety acids, are valuable but difficult obtain catalysis, generated in an enantioconvergent version. This new methodology features good functional group tolerance, easy scale‐up, facile transformation and avoids cumbersome steps, handling organometallic reagents using stoichiometric materials. Mechanistic investigations indicate process induced nickel catalysis.

Language: Английский

Citations

16

Electrochemical E-Selective Semireductive Dicarboxylation of Aryl Alkynes with CO2 DOI
Lan Zhao, Wen‐Jun Xie, Zheng-Zheng Meng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3241 - 3246

Published: April 5, 2024

Herein, we report an electrochemical protocol for the dicarboxylation of aryl alkynes using CO2. With a graphite rod as cathode and Al sacrificial anode, series valuable butenedioic acids are obtained in moderate to excellent yields with E/Z ratio up 50:1. This method features high E-selectivity, step atom economy, easy scalability, nice substrate scope, which renders it appealing promising applications organic synthesis materials chemistry.

Language: Английский

Citations

10

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

2

Asymmetric Multicomponent Propargylations via Carbon Dioxide Shuttling and Fixation DOI

Zi‐Han Li,

Jiang-Shan Ma,

Han-Yu Lu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(15), P. 11646 - 11656

Published: July 22, 2024

Language: Английский

Citations

7

Visible Light Photoredox-Catalyzed Formyl/Carboxylation of Activated Alkenes with Glyoxylic Acid Acetals and CO2 DOI

Yang Han,

Yang Yao,

Qi Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(20), P. 4194 - 4199

Published: May 15, 2024

A photoredox-catalyzed sequential α-formyl/carboxylation of alkenes with glyoxylic acid acetals and CO

Language: Английский

Citations

6

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

6

Synergistic Photoredox/Palladium Catalyzed Enantioconvergent Carboxylation of Racemic Heterobiaryl (Pseudo)Halides with CO2 DOI

Bihai Ye,

Lei Su,

Kaiting Zheng

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 64(1)

Published: Aug. 16, 2024

Herein, we report a synergistic photoredox/palladium catalytic system for the efficient enantioconvergent synthesis of axially chiral esters from racemic heterobiaryl (pseudo)halides (bromides/triflates) with CO

Language: Английский

Citations

5

Visible-Light-Promoted Cascade Carboxylation/Arylation of Unactivated Alkenes with CO2 for the Synthesis of Carboxylated Indole-Fused Heterocycles DOI

Yang Han,

Qi Yang,

Yang Yao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6341 - 6346

Published: July 18, 2024

Described here is a visible-light-promoted cascade carboxylation/arylation of indole-tethered unactivated alkenes with CO

Language: Английский

Citations

4

Tandem asymmetric propargylic amination/carboxylative cyclization reaction to chiral 5-methylidene-2-oxazolidinones using CO2 as C1 synthon DOI
Zheng Zhang, Zhihao Zhang, Ying Sun

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 4, 2024

Language: Английский

Citations

4