Oxidative [4 + 2] annulation of 1-naphthols with alkynes accelerated by an electron-deficient rhodium(<scp>iii</scp>) catalysts

Dias, Antônio Junio Araujo; Takahashi, Hiroto; Nogami, Juntaro; Nagashima, Yuki; Tanaka, Ken

doi:10.1039/d1ob02181h

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2022

2024

Publication Types

Select...

Article3

Book1

Relationship

Self Cite0

Independent4

Authors

Journals

Cited by 4 publications

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation

et al. 2022

View full text Add to dashboard Cite

The hydroxyl‐directed iridium‐catalyzed peri‐selective C−H bond activation to synthesize substituted pyrano[2,3,4‐de]chromen‐2‐ones and further chalcogenylation under blue light irradiation has been realized efficiently. Most products of polycyclic pyrans and corresponding chalcogenated derivatives with various substituents were achieved in good to excellent yields. Preliminary mechanistic studies suggest that this transformation may pass through a five‐membered iridacycle intermediate containing an O−Ir σ‐bond and a photocatalytic free radical process.

show abstract

Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation

et al. 2022

View full text Add to dashboard Cite

show abstract

Iridium‐Catalyzed Electrooxidative Annulation of Naphthol with Acrylate via C−H Bond Activation for the Synthesis of Naphtho[1,8‐bc]furan

Patil,

Das,

Bhanage

2024

Eur J Org Chem

View full text Add to dashboard Cite

Iridium catalyzed electrochemical coupling of naphthols with acrylates for the syntheses of naphtho[1,8‐bc]furan derivatives are herein reported. Ir‐catalyzed electrochemical C‐H annulation is accomplished within a supportive catalysis manifold, paving the way for electrooxidative C‐H acrylation via weak O‐coordination. The merge of iridium catalysts and electric current not only minimizes the need for a stoichiometric amount of chemical oxidants but also confirms broad reaction compatibility with a variety of electronically and sterically diverse substrates. This utility provides a valuable method for producing a wide range of naphtho[1,8‐bc]furan derivatives in good to moderate yields.

show abstract

Six-membered ring systems: With O and/or S atoms

Santos,

Silva

2023

Progress in Heterocyclic Chemistry

View full text Add to dashboard Cite

Oxidative [4 + 2] annulation of 1-naphthols with alkynes accelerated by an electron-deficient rhodium(iii) catalysts

Abstract: The 1,3-diethoxycarbonyl-2,4,5-trimethylcyclopentadienyl (CpE) rhodium(III) complex displayed high efficacy in the catalytic oxidative annulation of 1-naphthols with internal alkynes under mild conditions. DFT calculations revealed that lower activation energies for the...

Cited by 4 publications

References 35 publications

Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation

Hydroxyl‐Directed Iridium‐Catalyzed Synthesis of Pyrano[2,3,4‐de]chromen‐2‐ones and Further Chalcogenation under Blue‐Light Irradiation

Iridium‐Catalyzed Electrooxidative Annulation of Naphthol with Acrylate via C−H Bond Activation for the Synthesis of Naphtho[1,8‐bc]furan

Six-membered ring systems: With O and/or S atoms

Contact Info

Product

Resources

About