Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines DOI
Ran Ding, Gang Dong, Xu Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15733 - 15738

Published: Oct. 16, 2024

Remarkable progress has been made in the radical cascade cyclization of heteroaryl- or aryl-tethered alkenes to construct benzene-fused frameworks via cracking aryl C–H bonds. In contrast, linear dienes through vinyl bonds nonbenzene-fused ring with endocyclic double significantly lagged behind, and major advances have largely restricted generation 5-membered heterocycles, such as pyrrolinones. Herein, we report silver-mediated regioselective sulfonylation-cyclization sodium sulfinates form sulfonylated 6- 7-membered cyclic enamines.

Language: 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

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 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.

Language: Английский

Citations

1
Regioselective tandem sulfonylation/cyclization of unsaturated N-substituted enamides with sulfonyl chlorides by copper catalysis DOI
Ran Ding, Tao Wu, Tao Ma

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5784 - 5790

Published: Jan. 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.

Language: Английский

Citations

2
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

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(14), P. 5473 - 5473

Published: July 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.

Language: Английский

Citations

6
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
Visible‐light‐induced Regioselective Selenohydroxylation of Enamine Amides with Diaryl Diselenides DOI

Shiliang Jiang,

Yuting Leng, Panpan Wang

et al.

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

Published: July 26, 2024

Abstract This article reports the synthesis of alpha‐hydroxy‐beta‐seleno amides containing intramolecular hydrogen bonds by selective oxyselenization and double bond cleavage reactions enamine with diaryl diselenides under visible light irradiation. protocol proceeds well to provide 30 desired products yields 37 %–80 % using 12 W blue LED as source room temperature conditions. Moreover, plays a dual role substrate photoactive reagent, oxygen in air participates reaction, thus avoiding extra addition environmentally unfriendly photoctalysts oxidants.

Language: Английский

Citations

1
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

1
Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones DOI

Kaixia Sui,

Yuting Leng, Panpan Wang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(51), P. 11184 - 11189

Published: Dec. 12, 2024

A visible-light-induced radical cyclization of α-brominated amides has been developed to construct benzimidazole[2,1-

Language: Английский

Citations

1
Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines DOI
Ran Ding, Gang Dong, Xu Tang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15733 - 15738

Published: Oct. 16, 2024

Remarkable progress has been made in the radical cascade cyclization of heteroaryl- or aryl-tethered alkenes to construct benzene-fused frameworks via cracking aryl C–H bonds. In contrast, linear dienes through vinyl bonds nonbenzene-fused ring with endocyclic double significantly lagged behind, and major advances have largely restricted generation 5-membered heterocycles, such as pyrrolinones. Herein, we report silver-mediated regioselective sulfonylation-cyclization sodium sulfinates form sulfonylated 6- 7-membered cyclic enamines.

Language: Английский

Citations

0