Substituent-Dependent, Switchable Synthesis of Nonaromatic and Aromatic Heterocyclic Sulfones Using Visible Light DOI

Mithu Roy,

Itu Mallick,

Manas Mohan Mahapatra

и другие.

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9357 - 9362

Опубликована: Окт. 23, 2024

In this Letter, we described a visible-light-induced switchable synthesis of nonaromatic and aromatic sulfonyl heterocycles. The product selectivity between 2,5-dihydropyrrole pyrrole can be tuned by altering the substituent on N atom 1,6-diyne. We highlight intricacy efficiency approach in constructing molecular frameworks under mild conditions with high functional group tolerance. This study elucidates mechanism underlying selectivity, highlighting its potential as compelling alternative to traditional synthetic techniques.

Язык: Английский

Divergent Synthesis of Polysubstituted 1,2-Dihydropyridines and Pyridines through Manganese-Mediated Radical Cascade Cyclization of Tertiary Enamides DOI
Xiaoxu Chen, Sen Chen, Jiping Wang

и другие.

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

Опубликована: Янв. 28, 2025

A Mn(III)-mediated radical cascade cyclization of N-propargyl enamides with sodium sulfinates was developed. Mechanistic studies indicated that this process is mainly composed the chemoselective addition sulfonyl to C≡C bond and regioselective intramolecular 6-endo-trig cyclization. This protocol provided a powerful method for divergent synthesis diverse polysubstituted meta-sulfonylpyridines or 1,2-dihydropyridines just by varying solvent temperature featuring good functional group compatibility simple operation.

Язык: Английский

Процитировано

1

Multicomponent Reactions Based on SO2 Surrogates: Recent Advances DOI
Gang Chen, Zhong Lian

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(25)

Опубликована: Апрель 25, 2023

Abstract Compounds containing sulfonyl‐derived functional groups have received intensive attention owing to their widespread applications in life science, pharmaceuticals and materials science. To access this type of compounds, the multi‐component sulfonylation reactions relying on sulfur dioxide (SO 2 ) insertion strategy emerged as novel attractive approaches past decade. The utilization SO surrogates for multicomponent (MCRs) improved reaction flexibility step economy. Moreover, some advances been achieved challenging but practical asymmetric MCRs construction high value‐added chiral sulfones. This review aims summarize progress made involving from 2019 2022, point out potentials challenges field.

Язык: Английский

Процитировано

23

Electrochemical Sulfonylation/Cyclization of N-Alkenylacrylamides with Sodium Sulfinates or Sulfonyl Hydrazides DOI
Zhixian Yang,

Lu-Cai Ding,

Gui-Hong Yang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10660 - 10677

Опубликована: Июль 18, 2024

Two general protocols for the regioselective electrochemically enabled sulfonylation cyclization of

Язык: Английский

Процитировано

8

Access to chiral sulfones with an all-carbon quaternary stereocenter from sulfur dioxide DOI

Chunxi Huang,

Xuemei Zhang, Liping Luo

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4275 - 4283

Опубликована: Янв. 1, 2024

A copper-catalyzed enantioselective four-component reaction via the insertion of sulfur dioxide toward synthesis chiral sulfones bearing an all-carbon quaternary stereocenter at β position is reported.

Язык: Английский

Процитировано

3

Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis DOI
Ran Ding, Tao Wu, Tao Ma

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(20), С. 5784 - 5790

Опубликована: Янв. 1, 2024

The radical cascade cyclization of vinyl-tethered alkenes has become a promising tool for rapidly assembling nonbenzene-fused cyclic skeletons via the cracking alkenyl C–H bonds, but this approach been limited to generate five-membered rings.

Язык: Английский

Процитировано

3

Manganese(III)-Mediated Selective Cascade Phosphorylation-Cyclization of Tertiary Enamides for the Synthesis of Multi-Substituted 3-Phosphorylpyridines DOI
Xin‐Ming Xu, Sen Chen, Qian Liu

и другие.

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

Опубликована: Янв. 14, 2025

A novel regioselective manganese(III)-mediated radical cascade cyclization of N-propargyl enamides with various H-phosphine oxides, H-phosphinates and H-phosphonates was developed. Mechanistic studies show that the reaction is mainly composed selective addition phosphonyl to C≡C bond intramolecular 6-endo-trig vinyl radical. Utilizing this protocol, we successfully synthesized a diverse range 3-phosphorylpyridines in high efficiency good functional group compatibility simple operation.

Язык: Английский

Процитировано

0

Synthesis of meta-Sulfonylpyridines via Copper(II)-Catalyzed Cascade Sulfonylation/Cyclization/Aromatization of Tertiary Enamides with Sulfonylhydrazides DOI
Xin‐Ming Xu, Jiping Wang, Xiaoxu Chen

и другие.

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

Опубликована: Март 5, 2025

A copper(II)-catalyzed radical cascade reaction of N-propargyl enamides with sulfonyl hydrazides was developed, which provided an unprecedented method for the direct synthesis meta-sulfonylpyridines in high efficiency good functional group compatibility and simple operation. Mechanistic studies indicated that this tandem process might be composed addition, intramolecular cyclization oxidative aromatization.

Язык: Английский

Процитировано

0

Photoredox Catalyzed Three-component Tandem Cyclization of 1,5-Dienes with α-Keto Acids and Water to Access Pyrrolidinones DOI

Kaixia Sui,

Shiliang Jiang,

Yuting Leng

и другие.

Chemical Communications, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

An efficient visible-light-induced radical cascade cyclization of 1,5-dienes with α-keto acids and water to access diverse acylated pyrrolidinones was developed.

Язык: Английский

Процитировано

0

Photoredox-Catalyzed Synthesis of 3-Sulfonylated Pyrrolin-2-ones via a Regioselective Tandem Sulfonylation Cyclization of 1,5-Dienes DOI Creative Commons
Ran Ding, Liang Li,

Ya-Ting Yu

и другие.

Molecules, Год журнала: 2023, Номер 28(14), С. 5473 - 5473

Опубликована: Июль 17, 2023

A mild, visible-light-induced, regioselective cascade sulfonylation-cyclization of 1,5-dienes with sulfonyl chlorides through the intermolecular radical addition/cyclization alkenes C(sp2)-H was developed. This procedure proceeds well and affords a mild efficient route to range monosulfonylated pyrrolin-2-ones at room temperatures.

Язык: Английский

Процитировано

7

Copper-catalyzed ring-opening sulfonylation of cyclopropanols via the insertion of sulfur dioxide toward the synthesis of γ-keto aryl sulfones DOI
Shen Lin, Xuemei Zhang, Zhong Lian

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(13), С. 3239 - 3244

Опубликована: Янв. 1, 2023

A copper-catalyzed three-component sulfonylation reaction is presented. This protocol provides easy and straightforward access to structurally diverse γ-keto aryl sulfones with good yields, mild conditions, low catalyst loading, functional group tolerance.

Язык: Английский

Процитировано

6