Visible-Light-Driven Carboxylative 1,2-Difunctionalization of C═C Bonds with Tetrabutylammonium Oxalate DOI Creative Commons

Sai Wang,

Pei Xu, Zhitao Liu

и другие.

ACS Central Science, Год журнала: 2024, Номер 11(1), С. 46 - 56

Опубликована: Ноя. 15, 2024

Herein, we report a visible-light-induced charge-transfer-complex-enabled dicarboxylation and deuterocarboxylation of C═C bonds with oxalate as masked CO2 source under catalyst-free conditions. In this reaction, disclosed the first example that tetrabutylammonium could be able to aggregate aryl substrates via π–cation interactions form charge transfer complexes, which subsequently triggers single electron from oxalic dianion ammonium countercation irradiation 450 nm bule LEDs, releasing radical anions. Diverse alkenes, dienes, trienes, indoles, including challenging trisubstituted olefins, underwent anti-Markovnikov high selectivity access valuable 1,2- 1,4-dicarboxylic acids well indoline-derived diacids β-deuterocarboxylic mild The in situ generated CO2•– molecules anions both add bond without assistance any photocatalyst or additives, made reaction sustainable, clean, efficient.

Язык: Английский

Decatungstate‐Photocatalyzed Diastereoselective Dearomative Hydroalkylation of Indoles DOI Creative Commons

Emeric Montinho‐Inacio,

Damien Bouchet, Wei‐Yang Ma

и другие.

European Journal of Organic Chemistry, Год журнала: 2024, Номер 27(22)

Опубликована: Апрель 16, 2024

Abstract In this study, we present an efficient and straightforward dearomative hydroalkylation of indoles. By utilizing alkanes or ethers as alkyl radical sources employing TBADT a cost‐effective photocatalyst for direct hydrogen atom transfers (HAT), achieved successful conversion these heterocyclic derivatives into 2‐alkylindolines with good to excellent yields high diastereoselectivity under mild reaction conditions.

Язык: Английский

Процитировано

8
Photoredox-Neutral Deoxygenative Carboxylation of Acylated Alcohols with Tetrabutylammonium Oxalate DOI

Chen-Wei Xu,

Si-Yi Yan,

Hui Xu

и другие.

ACS Catalysis, Год журнала: 2024, Номер 14(16), С. 11967 - 11973

Опубликована: Июль 26, 2024

Herein, a photoredox-neutral strategy for carboxylation of acylated alcohols via C(sp3)–O bond activation and cleavage with tetrabutylammonium oxalate (TBAO) as the carbonyl source reductant well promoter is described. Neither pre-established CO2 atmosphere nor external electron donors are required TBAO crucial transformation. Various primary, secondary, tertiary could be smoothly converted to corresponding aryl acetic acids, which core structures diverse pharmaceutical drugs.

Язык: Английский

Процитировано

5
Formate Salts: The Rediscovery of Their Radical Reaction under Light Irradiation Opens New Avenues in Organic Synthesis DOI

Qing Shen,

Kun Cao,

Xiaoqing Wen

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер 366(21), С. 4274 - 4293

Опубликована: Авг. 17, 2024

Abstract Formates are abundantly available and inexpensive commodity chemical, widely used in laboratory industrial organic synthesis. promising hydrogen carrier green C1 source, have also been a subject of research as SET reductants recent years. Compared to the toxic flammable gas carbon monoxide, which serves formates easier handle, store, transport, more environmentally friendly. Therefore, studies radical reactions, formate is not only an ideal source carbonyl, great significance synthesize carboxyl compounds with various structures, but reductant for editing molecules either scientific or production. The activation conversion formate, reductant, very challenging hot field

Язык: Английский

Процитировано

4
Formate‐Mediated Synthesis of β‐Hydroxysulfides from Olefins and Thiosulfonates via EDA Complex Strategy under Visible Light Irradiation in Air DOI

Qing Shen,

Xiaoyan Peng,

Jiahong Sui

и другие.

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(23), С. 3129 - 3134

Опубликована: Авг. 13, 2024

Comprehensive Summary A visible‐light‐induced and efficient one‐pot synthesis of β ‐hydroxysulfides from olefins, thiosulfonates HCOOCs using an EDA complex strategy under air atmosphere at room temperature has been disclosed. plausible radical involved mechanism is proposed. During the reaction process, formates play a crucial role: first, as donors in complex; second, providers hydrogen source; third, by generating CO 2 •– to reduce peroxide intermediates, leading formation ‐hydroxysulfides. In contrast previously reported thiol‐oxygen co‐oxidation reactions, this simple sustainable approach features mild conditions, operational simplicity, odorless excellent functional group tolerance.

Язык: Английский

Процитировано

3
1‐Methylpyridine‐2(1H)‐thione Photocatalyzed Giese Reaction with N‐Hydroxyphthalimide Esters via Single Electron Transfer DOI Open Access

Lanting Li,

Yuzhuo Wang, Li Yuan

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 18, 2025

Comprehensive Summary We have developed a series of 1‐methylpyridine‐2(1 H )‐thione (MPT) analogues to be used as organocatalysts. The MPT catalysts are easily prepared and bench‐stable. In our previous work, we found that the ground‐state catalyst could act nucleophile generate primary radicals via an S N 2 pathway. However, this reaction was limited benzyl radicals. Herein, reported new catalytic property catalyst. photoexcited ( E (MPT ·+ /MPT*) = –1.60 V vs. Ag/AgCl in MeCN) reduce NHPI esters through single electron transfer process. Various carbon radicals, including radical, well primary, secondary tertiary alkyl generated easily. Notably, amino acids, peptide, pharmaceuticals, other biologically active molecules modified by using methodology showing potential synthetic utility method.

Язык: Английский

Процитировано

0
HDAC inhibitor SAHA triggers the production of previously undescribed sesquiterpenes and undergoes biotransformation by the fungus Robillarda sessilis from Verbena officinalis L. DOI

Liangxiu Liao,

Junguo Huang,

Zhu Tao

и другие.

Phytochemistry, Год журнала: 2025, Номер unknown, С. 114411 - 114411

Опубликована: Янв. 1, 2025

Язык: Английский

Процитировано

0
Visible-Light Photoredox-Catalyzed Carboxylation of Benzylic C(sp3)–O Bonds in Ethers with CO2 DOI
Jingwei Yang,

Chuan‐Kun Ran,

Wenjing Zhu

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Июнь 5, 2025

Although significant progress has been made in achieving site-selective C-O bond functionalization specific substrates, the selective cleavage and of C(sp3)-O bonds ethers remain a fundamental challenge synthetic chemistry. Herein, we present an efficient carboxylation method via photoredox-catalyzed benzylic with carbon dioxide (CO2). Diverse primary, secondary, tertiary benzyl undergo CO2 to generate valuable aryl acetic acids, including several drug molecules. This photocatalyzed reaction is operationally simple implement versatile for various ethers, exhibiting favorable compatibility diverse functional groups. Mechanistic studies indicate that single electron transfer (SET) reduction might be key generating highly reactive radical anion intermediate, which could another SET process carbanions CO2.

Язык: Английский

Процитировано

0
Nucleophilic Organocatalyst for Photochemical Carbon Radical Generation via SN2 Substitution DOI
Yuzhuo Wang,

Shiwen Fan,

Xinjun Tang

и другие.

Organic Letters, Год журнала: 2024, Номер 26(18), С. 4002 - 4007

Опубликована: Май 1, 2024

Photochemical generation of radicals is a powerful way to construct various molecules. But most these methods rely on initiators or the redox properties radical precursors. Herein, we report photochemical organic catalyst that reacts with benzyl halide generate carbon via an SN2 pathway. This nucleophilic can be easily prepared and bench-stable. The process does not halides, showing potential synthetic utility. Control experiments UV–vis spectroscopic analysis indicate substitution adduct key intermediate.

Язык: Английский

Процитировано

2
Photoinduced Radical Approach for Desulfurative Alkylation of Cysteine Derivatives to Make Unnatural Amino Acids DOI
Pei Xu, Yiqin Liu,

Hui-Xian Jiang

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Окт. 4, 2024

Unnatural amino acids (UAAs) are highly valuable molecules in organic synthesis, pharmaceutical sciences, and material science. Herein, we present a photocatalytic radical approach for desulfurative alkylation of cysteine derivatives with arenethiol as the hydrogen atom transfer catalyst making UAAs peptides. The formate salt, acting donor, situ generates reductive CO

Язык: Английский

Процитировано

2
Visible-Light-Driven Carboxylative 1,2-Difunctionalization of C═C Bonds with Tetrabutylammonium Oxalate DOI Creative Commons

Sai Wang,

Pei Xu, Zhitao Liu

и другие.

ACS Central Science, Год журнала: 2024, Номер 11(1), С. 46 - 56

Опубликована: Ноя. 15, 2024

Herein, we report a visible-light-induced charge-transfer-complex-enabled dicarboxylation and deuterocarboxylation of C═C bonds with oxalate as masked CO2 source under catalyst-free conditions. In this reaction, disclosed the first example that tetrabutylammonium could be able to aggregate aryl substrates via π–cation interactions form charge transfer complexes, which subsequently triggers single electron from oxalic dianion ammonium countercation irradiation 450 nm bule LEDs, releasing radical anions. Diverse alkenes, dienes, trienes, indoles, including challenging trisubstituted olefins, underwent anti-Markovnikov high selectivity access valuable 1,2- 1,4-dicarboxylic acids well indoline-derived diacids β-deuterocarboxylic mild The in situ generated CO2•– molecules anions both add bond without assistance any photocatalyst or additives, made reaction sustainable, clean, efficient.

Язык: Английский

Процитировано

2