Synthesis of γ-keto sulfones through sulfonylation/acylation of alkenes merging NHC- and photo-catalysis DOI

Xu Sun,

Gan Zhang, Bo Ye

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 569, P. 114563 - 114563

Published: Sept. 25, 2024

Language: Английский

Substituent-Controlled Regioselective Photoinduced Cyclization of N-Allylbenzamides with N-Sulfonylaminopyridinium Salts DOI
Changduo Pan,

Zixian Yang,

Xian Wu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(3), P. 494 - 499

Published: Jan. 12, 2023

The annulation reactions of N-allylbenzamides with N-sulfonylaminopyridinium salts were developed under metal-free photoinduced mild conditions. Substituent-controlled sulfonaminoarylation and sulfonaminooxylation benzamides realized: lead to benzosultams, while N-(2-phenylallyl)benzamides give sulfonamidylated oxazoline derivatives. Control experiments indicated that those undergo a radical pathway arylsulfonamidyl radicals as the intermediates. aryl C–H bond functionalization in was involved for first time benzosultams.

Language: Английский

Citations

24

Radical-mediated photoredox hydroarylation with thiosulfonate DOI

Xiaoyuan Wan,

Dahan Wang, Huawen Huang

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(19), P. 2767 - 2770

Published: Jan. 1, 2023

Radical-mediated photoredox hydroarylation reaction of unactivated alkenes using thiosulfonate compounds as key radical precursors to synthesize pyridyquinazolinone and pyrroloquinazolinone derivatives is described.

Language: Английский

Citations

23

Metal-Free Photoinduced Hydrocyclization of Unactivated Alkenes toward Ring-Fused Quinazolin-4(3H)-ones via Intermolecular Hydrogen Atom Transfer DOI

Zixian Yang,

Xian Wu,

Jie Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(10), P. 1683 - 1688

Published: March 8, 2023

A visible-light-induced hydrocyclization of unactivated alkenes was developed using 3CzClIPN as the photocatalyst to generate substituted α-methyldeoxyvasicinones and α-methylmackinazolinones in moderate good yields. An intermolecular hydrogen atom transfer with THF source involved. Mechanism studies indicated that intramolecular addition situ formed aminal radical alkene generated polycyclic quinazolinone.

Language: Английский

Citations

23

Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures DOI
Han Liu, Lei Wang, Jin‐Tao Yu

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

Citations

23

Visible‐Light‐Driven Cyclizations DOI Creative Commons
Emilia Oueis, Mirella Elkadi, Ramón Rios

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 635 - 697

Published: Jan. 13, 2024

Abstract In recent years, the interest to develop cyclizations promoted by visible light has been gaining a lot of attention due its sustainability aspect. this review, we summarize most important advances in period describing methods used generate different ring sizes, while focusing on mechanistic details these reactions.

Language: Английский

Citations

8

Photo-induced cyclization of olefinic amides towards sulfonamidylated iminoisobenzofurans and benzoxazines DOI
Changduo Pan,

Shipeng Luo,

Yechun Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(14), P. 3479 - 3484

Published: Jan. 1, 2023

A visible-light induced radical cyclization of olefinic amides with easily available N -sulfonylaminopyridinium salts towards iminoisobenzofurans and benzoxazines has been developed.

Language: Английский

Citations

16

Photocatalytic C(sp2)–H sulfamoylation of enamides: regio- and stereoselective construction of (E)-β-sulfamoyl enamides DOI

Ling-Li Liu,

Yechun Wu,

Xian Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5470 - 5477

Published: Jan. 1, 2023

A photocatalytic, regio- and stereoselective olefinic β-C–H sulfamoylation of enamides with commercially available sulfamoyl chlorides was developed.

Language: Английский

Citations

12

Photocatalytic cyclization of 3-(2-isocyanophenyl)quinazolin-4(3H)-ones for the construction of quinoxalino[2,1-b]quinazolinones DOI

Xian Wu,

Ling-Li Liu,

Chengli Xiang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(18), P. 2556 - 2559

Published: Jan. 1, 2024

3-(2-Isocyanophenyl)quinazolin-4(3 H )-ones were designed and synthesized as new building units for the construction of novel quinoxalino[2,1- b ]quinazolinones under mild, photocatalytic metal-free conditions.

Language: Английский

Citations

5

Visible-Light-Induced Radical Cascade Cross-Coupling via C(sp3)–H Activation and C–N/N–O Cleavage: Feasible Access to Methylenebisamide Derivatives DOI

Jinglan Lei,

Min Li, Qingqing Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2300 - 2305

Published: March 27, 2023

Here we report facile and manipulable access to methylenebisamide derivatives via visible-light-driven radical cascade processes incorporating C(sp3)–H activation C–N/N–O cleavage. Mechanistic studies reveal that a traditional Ir-catalyzed photoredox pathway novel copper-induced complex-photolysis are both involved, contributing activating the inert N-methoxyamides rendering valuable bisamides. This approach exhibits many advantages, including mild reaction conditions, broad scope functional group tolerance, competitive step economy. Given mechanistic plenitude operational simplicity, believe this package deal paves promising way for synthesis of nitrogen-containing molecules.

Language: Английский

Citations

10

Photoredox-Catalyzed Tandem Cyclization of Enaminones with N-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones DOI
Wenyu Hu, Xiaoqiong Diao, Jinwei Yuan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 644 - 655

Published: Dec. 13, 2023

A photoredox-catalyzed intermolecular tandem sulfonamination/cyclization of enaminones was realized by using N-aminopyridinium salts as the sulfonaminated reagents without transition-metal catalysts or bases. The reaction exhibits a broad scope and good functional group tolerance, yields, regioselectivity. Preliminary mechanistic studies support radical property involvement N-centered intermediates.

Language: Английский

Citations

10