Iridium‐Catalyzed [4+2] Annulations of β‐Keto Sulfoxonium Ylides and <i>o</i>‐Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives

Wang, Xiao‐Tong; Song, Jia‐Lin; Zhong, Ming; Kang, Hua‐Jie; Xie, Hongmei; Che, Tong; Shu, Bing; Peng, Dongming; Zhang, Luyong; Zhang, Shang‐Shi

doi:10.1002/ejoc.202000411

Cited by 16 publications

(5 citation statements)

References 63 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Synthesis of 2‐(4‐(trifluoromethoxy)phenyl)quinoxaline (HL 3 ) : [65] The ligand was prepared similarly from 2‐bromo‐1‐(4‐(trifluoromethoxy)phenyl)ethan‐1‐one (0.693 g, 2.45 mmol) and 1,2‐phenylenediamine (0.291 g, 2.69 mmol) to give the product as pale yellow crystals. Yield=0.184 g, 26 %.…”

Section: Methodsmentioning

confidence: 99%

“…6, 141.5, 132.3, 131.4, 131.1, 130.4, 130.3, 129.8, 129.4, 127.8, 121.5, 120.5 (q, 1 J CF = 259.0 Hz) ppm. 19 3 ): [65] The ligand was prepared similarly from 2-bromo-1-(4-(trifluoromethoxy)phenyl)ethan-1-one (0.693 g, 2.45 mmol) and 1,2-phenylenediamine (0.291 g, 2.69 mmol) to give the product as pale yellow crystals. Yield = 0.184 g, 26 %.…”

Section: Synthesis Of the Substituted 2-phenylquinoxaline Ligandsmentioning

confidence: 99%

See 1 more Smart Citation

Organometallic Platinum(II) Photosensitisers that Demonstrate Ligand‐Modulated Triplet‐Triplet Annihilation Energy Upconversion Efficiencies

Fitzgerald

Xiao

Zhao

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

A series of 2-phenylquinoxaline ligands have been synthesised that introduce either CF 3 or OCF 3 electron-withdrawing groups at different positions of the phenyl ring. These ligands were investigated as cyclometalating reagents for platinum(II) to give neutral complexes of the form [Pt(C^N)(acac)] (in which C^N = cyclometalating ligand; acac = acetyl acetonate). X-ray crystallographic studies on three examples showed that the complexes adopt an approximate square planar geometry. All examples revealed strong PtÀ Pt linear contacts of 3.2041(6), 3.2199(3) and 3.2586(2) Å. The highly coloured complexes display efficient visible absorption at 400-500 nm (ɛ � 5000 M À 1 cm À 1 ) and orange red photoluminescent characteristics (λ em = 603-620 nm; Φ em � 37 %), which were subtly tuned by the ligand. Triplet emitting character was confirmed by microsecond luminescence lifetimes and the photogeneration of singlet oxygen with quantum efficiencies up to 57 %. Each complex was investigated as a photosensitiser for triplet-triplet annihilation energy upconversion using 9,10-diphenylanthracene as the annihilator species: a range of good upconversion efficiencies (Φ UC 5.9-14.1 %) were observed and shown to be strongly influenced by the ligand structure in each case.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of the Substituted 2-phenylquinoxaline Ligandsmentioning

confidence: 99%

Organometallic Platinum(II) Photosensitisers that Demonstrate Ligand‐Modulated Triplet‐Triplet Annihilation Energy Upconversion Efficiencies

Fitzgerald

Xiao

Zhao

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“… [60a] Recently, Zhang, et al . reported iridium‐Catalyzed [4+2] annulations of β ‐keto sulfoxonium ylides with o ‐phenylenediamines for the synthesis of quinoxaline derivatives [60b] …”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

2022

View full text Add to dashboard Cite

In recent years, the transition‐metal‐catalyzed functionalization reactions of sulfoxonium ylides have been explored extensively because of their usefulness as carbene‐transfer agents, since they can produce metal carbenes through metal catalysis. Moreover, they are safer and have the advantages of simple handling and good stability over their other counterparts like diazo‐compounds. This review article attempts to highlight the recent advances in the metal‐catalyzed C−H functionalization of sulfoxonium ylides.

show abstract

“…More recently, Rh(III)‐catalyzed C−H functionalization of 2‐arylindoles with sulfoxonium ylides has been reported for the synthesis of fused benzo[ a ]carbazoles and indolo[2,1‐ a ]isoquinolines. [14] Very recently, the coupling of 1,2‐diamines with sulfoxonium ylides has been reported for the synthesis of quinoxaline derivatives [15] . Interestingly, α‐aryl ketones have been prepared through the coupling of sulfoxonium ylides with arynes [16] .…”

Section: Introductionmentioning

confidence: 99%

Rh(III)‐Catalyzed Oxidative Annulation of 2‐Arylindazoles with β‐Ketosulfoxonium Ylides

et al. 2021

View full text Add to dashboard Cite

The Rh(III)‐catalyzed ortho‐C−H bond functionalization of 2‐aryl indazoles with β‐ketosulfoxonium ylides has been developed for the synthesis of 6‐arylindazolo[2,3‐a]quinoline derivatives in good to excellent yields with a broad substrate scope and good functional group tolerance. The reaction proceeds through a sequential ortho‐alkylation followed by cyclodehydration. The combination of 5 mol% of Cp*Rh(III) and 40 mol% AgSbF6 was found to be effective for this conversion.

show abstract

Iridium‐Catalyzed [4+2] Annulations of β‐Keto Sulfoxonium Ylides and o‐Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives

Cited by 16 publications

References 63 publications

Organometallic Platinum(II) Photosensitisers that Demonstrate Ligand‐Modulated Triplet‐Triplet Annihilation Energy Upconversion Efficiencies

Organometallic Platinum(II) Photosensitisers that Demonstrate Ligand‐Modulated Triplet‐Triplet Annihilation Energy Upconversion Efficiencies

Recent Advances in Metal‐Catalyzed C−H Bond Functionalization Reactions of Sulfoxonium Ylides

Rh(III)‐Catalyzed Oxidative Annulation of 2‐Arylindazoles with β‐Ketosulfoxonium Ylides

Contact Info

Product

Resources

About