Synthesis of 10-PhenanthrenolsviaPhotosensitized Triplet Energy Transfer, Photoinduced Electron Transfer, and Cobalt Catalysis DOI
Junli Li, Xiu‐Long Yang, Shigang Shen

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(24), P. 16458 - 16472

Published: Nov. 28, 2022

Due to the inert redox activity and high triplet energy, radical chemistry of 1,3-dicarbonyl compounds usually requires prefunctionalization substrates, external oxidant, high-energy UV light. Here, we report a visible-light-driven photocatalyst/cobaloxime system composed photosensitized energy transfer reaction (PEnT) photoinduced electron (PET) with an interrupted 6π-photocyclization/dehydrogenative aromatization in one pot synthesize 10-phenanthrenols. Preliminary mechanistic studies revealed that fac-Ir(ppy)3 plays dual roles catalysis for photocycloaddition via 1,2-biradical intermediates photoredox/cobaloxime dehydrogenative 1,4-biradical rather than 6π photocyclization tandem reaction. In contrast previous well-established compounds, provide new strategy activation under visible light catalysis, affording novel cyclization extremely atom economy synthesis

Language: Английский

Redox-neutral ketyl radical coupling/cyclization of carbonyls withN-aryl acrylamides through consecutive photoinduced electron transfer DOI
Zhonghua Qu,

Tong Tian,

Yongbo Tan

et al.

Green Chemistry, Journal Year: 2022, Volume and Issue: 24(19), P. 7403 - 7409

Published: Jan. 1, 2022

Redox-neutral ketyl couplings: a metal- and additive-free ConPET photocatalytic system allows highly efficient coupling/cyclization of N -aryl acrylamides carbonyls with formal 100% atom economy.

Language: Английский

Citations

61
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
Visible light-mediated radical-cascade addition/cyclization of arylacrylamides with aldehydes to form quaternary oxindoles at room temperature DOI

Zhaozhao Sun,

Huawen Huang, Qiaolin Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(13), P. 3506 - 3514

Published: Jan. 1, 2022

The visible light-induced oxidative radical cascade coupling of N -arylacrylamides with aldehydes using bromide as the hydrogen atom transfer agent to synthesize functional oxindoles is described.

Language: Английский

Citations

30
Visible-Light-Induced Cascade Arylazidation of Activated Alkenes with Trimethylsilyl Azide DOI

Xinzhuang Wu,

Xinyi Zhang, Xiaochen Ji

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(27), P. 5162 - 5167

Published: June 29, 2023

A visible-light-induced cascade arylazidation of activated alkenes with trimethylsilyl azide (TMSN3) has been developed. Mechanistic investigations reveal that the single electron transfer (SET) TMSN3 excited photocatalyst was involved in initial step, followed by radical addition/aryl migration/desulfonylation to furnish valuable α-aryl-β-azido amides and azidated oxindoles under mild conditions, which are versatile building blocks organic synthesis. With simple treatment, obtained arylazidated products were further converted β-amino amide 1,2,3-triazole derivatives.

Language: Английский

Citations

17
Metal-free synthesis of carbamoylated dihydroquinolinones via cascade radical annulation of cinnamamides with oxamic acids DOI

Pallav Suman,

Kirti Tomar,

Chandra Shekhar Nishad

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(9), P. 1821 - 1833

Published: Jan. 1, 2024

Metal-free synthesis of medicinally important carbamoylated dihydroquinolinones using readily available, cheap and environment-friendly materials with good to excellent yields.

Language: Английский

Citations

6
Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift DOI

Yongbo Tan,

Jing Zhao, Guo‐Jun Deng

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(12), P. 2398 - 2402

Published: March 18, 2024

Herein, we introduce a tetralone-mediated photocyclization method of N-arylacrylamides. The protocol proceeds smoothly to deliver diverse set 3,4-dihydroquinolinones in moderate good yields with excellent functional group compatibility and readily allows for late-stage modifications number complex drug molecules. Mechanistic studies reveal that the present systems ultraviolet light irradiation enable cyclization via energy transfer exclusive 1,3-hydrogen shift.

Language: Английский

Citations

6
Catalytic Enantioselective 6π Photocyclization of Acrylanilides DOI Creative Commons

Benjamin A. Jones,

Pearse Solon, Mihai V. Popescu

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 145(1), P. 171 - 178

Published: Dec. 26, 2022

Controlling absolute stereochemistry in catalytic photochemical reactions is generally challenging owing to high rates of background reactivity. Successful strategies broadly rely on selective excitation the reaction substrate when associated with a chiral catalyst. Recent studies have demonstrated that Lewis acid complexes can enable energy transfer from photosensitizer facilitate enantioselective triplet state reactions. Here, we apply this approach catalysis 6π photocyclization through design an iridium optimized undergo only presence complex. Among group iridium(III) sensitizers, enantioselectivity and yield closely correlate photocatalyst within narrow window enabled by modest reduction upon binding scandium/ligand These results demonstrate tuning offers means suppress reactivity improve

Language: Английский

Citations

24
Endo/Exo-Controllable Photocyclization by EnT-SET-Switch DOI

Xian-Peng Cai,

Bin-Hong Han,

Fu-Tong Cen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(16), P. 2863 - 2867

Published: April 17, 2023

CBZ6, a redox-neutral non-donor-acceptor-type organo-photocatalyst, presents strong reductive potential with an oxidative of -2.16 V (vs SCE). It can work as photosensitizer for both single-electron transfer and triplet energy processes. This feature enables site-selective control in the intramolecular hydroarylation acrylamides. Both 5-exo-trig 6-endo-trig cyclization products could be prepared regiospecfically under mild conditions. No transition metal, halogen-containing reagents, or additional reductant oxidant is involved. process provides concise environmentally sustainable access to series oxindoles dihydroquinolinones.

Language: Английский

Citations

13
Recent Advances for the Synthesis of Dihydroquinolin-2(1H)-ones via Catalytic Annulation of α,β-Unsaturated N-Arylamides DOI Open Access
Yan‐Ning Niu,

Lin-shuang Tian,

Huai-Zhong Lv

et al.

Catalysts, Journal Year: 2023, Volume and Issue: 13(7), P. 1105 - 1105

Published: July 15, 2023

Dihydroquinolin-2(1H)-ones (DHQOs) represent a class of valuable bioactive compounds with six-membered nitrogen-containing heterocyclic structures. The development simple, mild, and efficient synthetic methods has been widely considered by chemists. In this review, we have summarized series different strategies for the synthesis DHQOs via catalytic annulation α,β-unsaturated N-arylamides in past decade, including covering electrophilic cyclization, radical initiated photochemical cyclization reactions. Additionally, substrate scope mechanistic details are also discussed. This paper provides useful reference diverse methodologies DHQO.

Language: Английский

Citations

12
Photocatalytic Charge-Transfer Complex Enables Hydroarylation of Alkenes for Heterocycle Synthesis DOI

Ying‐Zheng Ren,

Chang-Zhen Fang,

Beibei Zhang

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(19), P. 3585 - 3589

Published: May 8, 2023

Here, we report a photocatalytic charge-transfer complex (CTC) strategy for one electron reduction of alkenes using thiolate as catalytic donor. This CTC system could engage hydroarylation both activated and unactivated the synthesis various heterocycles. The reactions do not require any photocatalysts or acids are easy to perform. Mechanistic studies revealed formation between alkene.

Language: Английский

Citations

8