Selective 1,2‐Carboimination of Isothiocyanates to Access S‐Substituted Isothioureas via Energy Transfer Catalysis DOI

Li‐Ning Chen,

S. K. Liang,

Juan Luo

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 5, 2024

Abstract Herein, we introduce a novel method for the synthesis of S ‐substituted isothiourea compounds via selective 1,2‐carboimination between oxime esters as bifunctional reagents and C=S bond isothiocyanates under visible‐light catalysis. This approach deviates from conventional methods by precisely modulating substrate electronics to selectively functionalize over C=N bond, eliminating need strong bases high temperatures bypassing formation thiourea intermediates. Consequently, this protocol enables efficient one‐step ‐alkyl isothioureas, with featuring mild reaction conditions, operational simplicity broad scope.

Язык: Английский

Visible-Light-Induced Energy-Transfer-Mediated Hydrofunctionalization and Difunctionalization of Unsaturated Compounds via Sigma-Bond Homolysis of Energy-Transfer Acceptors DOI
Qiao Sun, Shaopeng Wang, Yuan Xu

и другие.

ACS Catalysis, Год журнала: 2025, Номер 15(3), С. 1854 - 1941

Опубликована: Янв. 17, 2025

Over the past decade, visible-light-mediated energy-transfer (EnT) catalysis, particularly triplet–triplet (TTEnT) has emerged as a mild and environmentally friendly approach for diverse organic synthetic transformations. In contrast to photoredox which typically requires sacrificial electron donors or acceptors complete catalytic cycle, EnT photocatalysis generally proceeds with high atom economy while minimizing generation of wasteful byproducts. Furthermore, successful catalysis is contingent upon precise control redox potentials both photocatalysts substrates, strategies are primarily influenced by triplet energy compatibility between these entities. Considering growing importance photocatalysis, well hydrofunctionalization difunctionalization reactions in synthesis, this review systematically summarizes significant advancements EnT-enabled unsaturated compounds via sigma-bond homolysis over decade. Special emphasis placed on elucidating substrate scopes mechanistic scenarios. Additionally, discusses versatile applications methodologies addresses current challenges opportunities within evolving research field. This structured into six main categories based different types sigma-bonds undergoing homolysis. These include transformations mediated 1) N–O bond oxime esters other N,O-radical precursors; 2) N–S N-sulfonyl imines N,S-radical 3) chalcogen–chalcogen disulfides oxy/thio/selenosulfonates; 4) C–S tri/difluoromethylated sulfinates, acetylenic triflones, arylsulfonium salts; 5) C–X (X = halogen) halides; 6) acceptors. Through providing theoretical backgrounds along comprehensive overview currently employed acceptors, photosensitizers, contemporary EnT-induced compounds, aims serve an invaluable resource future innovations rapidly

Язык: Английский

Процитировано

3

Visible-Light-Induced Decarboxylative Aminosulfonylation of (Hetero)aryl Carboxylic Oxime Esters DOI

Zhen Zhuang,

Yuting Sun, Yuanchen Zhong

и другие.

Organic Letters, Год журнала: 2024, Номер 26(3), С. 713 - 718

Опубликована: Янв. 12, 2024

Sulfonamides are important structures in pharmaceuticals, agrochemicals, and organocatalysts, yet the rapid benign synthesis of these compounds is still a great challenge. Herein we report photoinduced method for synthesizing sulfonamides from (hetero)aryl carboxylic acid oxime esters. This reaction proceeds via one-pot cascade radical–radical cross-coupling by energy-transfer-mediated photocatalysis. A wide substrate scope including substrates late-stage modification pharmaceutical molecular entities reveal its generality.

Язык: Английский

Процитировано

14

Photocatalyzed C3-α-aminoalkylation of quinoxalin-2(1H)-ones with amino acid-derived oxime esters under metal-free conditions DOI
Bin Wang,

Runye Gao,

Xiao Geng

и другие.

Molecular Catalysis, Год журнала: 2025, Номер 573, С. 114795 - 114795

Опубликована: Янв. 5, 2025

Язык: Английский

Процитировано

2

Development of a Phototriggered Diradical Phosphoamination Strategy of Alkenes DOI

Apurba Samanta,

Partha Pratim Mondal,

Goutam Bej

и другие.

Organic Letters, Год журнала: 2025, Номер 27(2), С. 606 - 611

Опубликована: Янв. 6, 2025

Aminophosphonates serve as extremely important moieties with respect to their activities in biological systems. However, incorporating a Nitrogen and Phosphorus moiety by conventional techniques ionic mode is usually associated extensive prefunctionalization of the substrates, employing harsh conditions reagents that limit viability these methods. Introducing both components radicals may be viable option. We hereby propose an overhaul existing reactivity paradigm demonstrating photocatalytic diradical-based approach, where new iminophosphonating are rationally designed developed used extensively homolytic cleavage for simultaneously installing iminyl phosphonyl groups onto alkenes.

Язык: Английский

Процитировано

1

Metal-free photosensitized aminosulfonylation of alkenes: a practical approach to β-amido sulfones DOI
Meiling Chen,

Wenyan Sun,

Jingjing Yang

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(10), С. 3857 - 3863

Опубликована: Янв. 1, 2023

A general and environmentally friendly organic photo-induced strategy was developed for the synthesis of diverse alkyl-substituted β-amino sulfone derivatives, including primary, secondary, tertiary products.

Язык: Английский

Процитировано

20

Photoinduced Difunctionalization of Diazenes Enabled by N–N Radical Coupling DOI

Yu‐Shi Jiang,

Shanshan Li,

Xue-Ling Luo

и другие.

Organic Letters, Год журнала: 2023, Номер 25(36), С. 6671 - 6676

Опубликована: Авг. 29, 2023

In this study, a metal-free difunctionalization strategy for diazenes was developed using range of bifunctionalization reagents. This involves unique N(sp3)–N(sp2) radical coupling between the hydrazine and imine radical. More than 30 triazane core motifs were constructed by installing imines various functional groups, including alkyl, phenyl, cyanoalkyl, sulfonyl on both ends nitrogen–nitrogen bond in an efficient manner.

Язык: Английский

Процитировано

17

Photocatalytic vinyl radical-mediated multicomponent 1,4-/1,8-carboimination across alkynes and olefins/(hetero)arenes DOI
Shanshan Li,

Yu‐Shi Jiang,

Xue-Ling Luo

и другие.

Science China Chemistry, Год журнала: 2023, Номер 67(2), С. 558 - 567

Опубликована: Сен. 27, 2023

Язык: Английский

Процитировано

15

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

Yuwei Hong

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 11(4), С. 1232 - 1250

Опубликована: Дек. 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.

Язык: Английский

Процитировано

15

The Merger of Halogen Atom Transfer (XAT) and Energy Transfer Catalysis (EnT) for the Modular 1,2-Iminylalkylation of Diazenes DOI
Shanshan Li,

Yu‐Shi Jiang,

Li-Ning Chen

и другие.

Organic Letters, Год журнала: 2023, Номер 25(38), С. 7009 - 7013

Опубликована: Сен. 14, 2023

The 1,2-iminylalkylation of diazenes using alkyl iodides in combination with an O-benzoyl oxime is reported. In this transformation, acted as a radical precursor and XAT mediator. addition to common iodides, other such iodomethane, iodomethane-d3, trifluoroiodomethane, ethyl difluoroiodoacetate, iodoalkanes containing unprotected hydroxyl amide groups can also serve C-radical precursors the electrophilic acceptors.

Язык: Английский

Процитировано

13

Advancements in visible-light-induced reactions via alkenyl radical intermediates DOI
Helena F. Piedra, Manuel Plaza

Photochemical & Photobiological Sciences, Год журнала: 2024, Номер 23(6), С. 1217 - 1228

Опубликована: Май 3, 2024

Язык: Английский

Процитировано

4