Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes DOI
Yingchun Ma,

Ping Yu,

Ruoyu Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Language: Английский

Visible-light induced direct C(sp3)–H functionalization: recent advances and future prospects DOI
Jia‐Lin Tu, Yining Zhu, Pengcheng Li

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5278 - 5305

Published: Jan. 1, 2024

This review summarizes the latest methodological advances in photocatalytic C(sp 3 )–H functionalization, with a particular emphasis on formation of C–P, C–B, C–S bonds, etc ., and some prominent efforts asymmetric C–H functionalization.

Language: Английский

Citations

17
Electrophotocatalysis Versus Indirect Electrolysis: Electrochemical Selenocyclization of 3‐Aza‐1,5‐dienes Facilitated by Energy Transfer, Direct Photolysis or N‐Hydroxyphthalimide DOI

Dongyin Wang,

Li Zeng, Jifu Shi

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(36)

Published: April 23, 2024

Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for selenylation/cyclization of fragile substrates 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions indirect electrolysis one both regioselective external-oxidant- transition-metal-free, associated a broad substrate scope high Se-economy, all three methods amenable gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments all-solar-driven syntheses.

Language: Английский

Citations

6
Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides DOI
Yan‐Ning Niu, Keyu Wang, Fuzhong Han

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134497 - 134497

Published: Jan. 1, 2025

Language: Английский

Citations

0
α-Thiocyanation of Enol Acetates and Sodium Thiocyanate under Electrochemical Conditions DOI
Jinpeng Zhang, Yuliang Qian, Man Ning

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(1), P. 189 - 189

Published: Jan. 1, 2025

Language: Английский

Citations

0
Convergent and Divergent Synthesis of Dihydroisoquinoline-1,4-diones Enabled by a Photocatalytic Skeleton-Editing [4+2] Strategy DOI Creative Commons

Hai‐Wu Du,

Junsong Jia, Xiaoyi Chen

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Dihydroisoquinolinediones are ubiquitous nitrogen-containing fused heterocyclic units in natural products, drug molecules, and functional materials. However, straightforward synthesis of dihydroisoquinolinediones from simple readily available precursors remains challenging underdeveloped. Herein, we developed an unprecedented photocatalytic [4 + 2] skeleton-editing strategy enabled direct dihydroisoquinoline-1,4-diones vinyl azides carboxylic NHPI esters. The key to success is the use NHPIs as bifunctional reagents skeleton-edit cyclization cascade. Notably, serve α-primary amino alkyl radicals followed by a radical initiated ring-enlargement event. Impressively, reaction provides convergent access identical dihydroisoquinolinedione different divergent NHPI. cleaves two C-N bonds forges one bond, C-C ring.

Language: Английский

Citations

0
Electroreductive Carboxylation of Benzylphosphonium salts with CO2 Through the Cleavage of the C(sp3)-P Bond DOI

Fen Han,

Fenfen Xie,

Mengyun Yin

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(28), P. 5724 - 5728

Published: Jan. 1, 2024

Herein, a novel electroreductive carboxylation of benzylphosphine salts with CO 2 through cleavage the C(sp 3 )-P bond was reported under conditions without redox reagents and noble metal catalysts.

Language: Английский

Citations

2
Organophotocatalytic Regioselective Silylation/Germylation and Cascade Cyclization of N-Alkenyl α-CF3 Acrylamides: Access to Densely Functionalized 4-Pyrrolin-2-ones DOI

Kalu Ram Bajya,

Shivam Maurya, Sermadurai Selvakumar

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(43), P. 9269 - 9275

Published: Oct. 21, 2024

We report an organophotoredox-catalyzed silylation/germylation cascade cyclization of

Language: Английский

Citations

2
Photocatalytic Regioselective Tandem Cyclization Protocol to Trifluoromethylated Pyrrolidones DOI Open Access
Panpan Wang, Yuting Leng,

Kaixia Sui

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 21, 2024

Abstract A new environmentally friendly and efficient strategy for preparing trifluoromethylated pyrrolidones has been developed. The process involves using visible light to induce radical cyclization of 1,5‐dienes with CF 3 SO 2 Na, resulting in excellent regioselectivity. This method uses less expensive easy‐to‐store trifluoromethylation reagents, making it an attractive option. Additionally, the can be easily modified preliminary mechanistic studies have presented.

Language: Английский

Citations

2
DABCO‐Mediated Photoelectrochemical Three‐Component Sulfonocyclization of 3‐Aza‐1,5‐dienes DOI

Lu-Cai Ding,

Gui-Hong Yang,

Li Luo

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

Comprehensive Summary Herein, we report a rare example of three‐component net‐oxidative sulfonylation SO 2 surrogate with an oxidatively activated radical precursor under mild and metal‐ external‐oxidant‐free conditions. The mildness sustainability the reaction are enabled by photoelectrocatalysis, 3‐aza‐1,5‐dienes, organotrifluoroborates 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) undergo sulfonylative cyclization to afford sulfono 4‐pyrrolin‐2‐ones in atom‐economical manner broad substrate scope good functional‐group tolerance. protocol is amenable late‐stage diversification complex molecular architectures as well gram‐scale synthesis. Sunlight could be used light source, conducted all‐solar mode using commercially available photovoltaic panel generate electricity situ . Mechanistic studies reveal that generated (DABCO), which was generally innocent previous reactions, functions electron shuttle between photocatalytic cycle reactants.

Language: Английский

Citations

2
Electrophotocatalytic Thiocyanation and Sulfonylation Cyclization of Unactivated Alkenes DOI
Yingchun Ma,

Ping Yu,

Ruoyu Qin

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 18, 2024

We report an electrophotocatalytic process that enables the thiocyanation and sulfonylation/cyclization of alkenes. It is applicable to a wide range unactivated alkenes, using inexpensive photocatalyst 2,4,6-triphenylpyrylium tetrafluoroborate (TPPT) produce diverse array heterocycles containing sulfonyl thiocyano groups with good functional group tolerance. The protocol operates under mild, chemical oxidant- transition-metal-free, broad scope substrates. Preliminary mechanistic studies suggest reaction involves combination electrolysis reductive quenching photocatalytic cycle TPPT.

Language: Английский

Citations

1