Palladium-catalyzed enol/enolate directed oxidative annulation: functionalized naphthofuroquinone synthesis and bioactivity evaluation

Lv, Shuaipeng; Liu, Haitao; Kang, Jie; Luo, Yun; Gong, Ting; Dong, Zihui; Sun, Guibo; He, Chun‐Nian; Sun, Xiaobo; Wang, Lei

doi:10.1039/c9cc05233j

Cited by 7 publications

(3 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2019, Wang and co‐workers synthesized naphthofuroquinone derivatives 95 and 96 from annulations of 2‐hydroxy‐1,4‐naphthoquinone 94 with internal alkynes 2 (Scheme 45). [48] For this purpose, they designed two reaction conditions. For the synthesis of 1,2‐naphthofuroquinones 95 , Pd(II) was served as a catalyst, oxone/benzoquinone (BQ) as oxidants and the reaction was carried out under O 2 .…”

Section: Transition Metal‐catalyzed Transformations Of Diaryl/alkyl A...mentioning

confidence: 99%

Transition Metal‐Catalyzed Dual C−H Activation/Annulation Reactions Involving Internal Alkynes

Doraghi,

Karimtabar,

Ghasemi

et al. 2024

The Chemical Record

View full text Add to dashboard Cite

Recently, transition metal‐catalyzed ortho‐C−H bond activation/annulations involving two internal alkyne molecules have been extensively used to synthesize highly substituted polycyclic aromatic scaffolds. Such reactions have emerged as a powerful atom and step‐economical strategy for the assembly of multifunctional bioactive molecules. In this context, we focused on the recent achievements of dual C−H bond activation/annulations, as well as functionalization reactions involving diaryl/alkyl alkynes.

show abstract

Section: Transition Metal‐catalyzed Transformations Of Diaryl/alkyl A...mentioning

confidence: 99%

Transition Metal‐Catalyzed Dual C−H Activation/Annulation Reactions Involving Internal Alkynes

Doraghi,

Karimtabar,

Ghasemi

et al. 2024

The Chemical Record

View full text Add to dashboard Cite

show abstract

“…Inspired by this result, they decided to investigate the reaction scope, employing several meta-substituted N-phenyl 2-trimethylsilylethynylbenzamides 47, bearing electrondonating and electron-withdrawing groups (R = H, Me, F, Br and Cl), and the respective products 48 were obtained in very good yields. In the same year, Wang, Sun, and co-workers reported the Pd(II)-catalyzed Oxonemediated oxidative sequential addition-annulation of 1,2-naphthofuroquinones 49 with diaryl alkynes 50, to prepare functionalized naphthofuroquinones 51 (Scheme 32) [37]. The method was efficiently applied to several functionalized 2-hydroxy-1,4-naphthoquinones 49, bearing electron-neutral, -donating, and -withdrawing aryl substituents.…”

Section: Oxygen-containing Heterocyclesmentioning

confidence: 99%

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

et al. 2021

View full text Add to dashboard Cite

Oxone is a commercially available oxidant, composed of a mixture of three inorganic species, being the potassium peroxymonosulfate (KHSO5) the reactive one. Over the past few decades, this cheap and environmentally friendly oxidant has become a powerful tool in organic synthesis, being extensively employed to mediate the construction of a plethora of important compounds. This review summarizes the recent advances in the Oxone-mediated synthesis of N-, O- and chalcogen-containing heterocyclic compounds, through a wide diversity of reactions, starting from several kinds of substrate, highlighting the main synthetic differences, advantages, the scope and limitations.

show abstract

“…89 In 2019, Sun, Wang, and co-workers presented a palladium-catalyzed oxidative annulation of naphthoquinones with internal alkynes(Scheme 21c). 90…”

Section: Scheme 20 Synthesis Of Dibenzofurans Via Rh Catalysismentioning

confidence: 99%

Directing-Group-Assisted Transition-Metal-Catalyzed Direct C–H Oxidative Annulation of Arenes with Alkynes for Facile Construction of Various Oxygen Heterocycles

et al. 2020

View full text Add to dashboard Cite

The most recent advances in the construction of oxygen heterocycles by the directing-group-assisted transition-metal-catalyzed direct oxidative annulation of arenes with diverse alkynes are summarized in this review. More than 140 recent research papers and many closely related reviews are referenced in this paper. Nine different oxygen heterocycles frameworks are discussed. Several traditional transition-metal catalysts as well as some classical non-noble metals are utilized to promote the annulation. Three plausible controlling models are disclosed to clarify the excellent regioselectivity outcomes achieved in case of unsymmetrical alkyne substrates.1 Introduction2 Coumarins3 I socoumarins and Their Analogues4 2-Pyrones and Their Analogues5 Chromones and Chroman-4-ones6 Chromenes and Isochromenes7 Fused Polycyclic Oxygen Heteroaromatics8 Benzofurans, Dihydrobenzofurans, and Furans9 Phthalides and Benzofuranones10 Benzoxepines11 Conclusion

show abstract

Palladium-catalyzed enol/enolate directed oxidative annulation: functionalized naphthofuroquinone synthesis and bioactivity evaluation

Abstract: Diverse naphthoquinone-containing heterocycle synthesis has been developed via enol/enolate-directed palladium catalytic processes together with late-stage functionalization and lead compound development.

Cited by 7 publications

References 37 publications

Transition Metal‐Catalyzed Dual C−H Activation/Annulation Reactions Involving Internal Alkynes

Transition Metal‐Catalyzed Dual C−H Activation/Annulation Reactions Involving Internal Alkynes

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

Directing-Group-Assisted Transition-Metal-Catalyzed Direct C–H Oxidative Annulation of Arenes with Alkynes for Facile Construction of Various Oxygen Heterocycles

Contact Info

Product

Resources

About