Ruthenium complexes of redox non-innocent aryl-azo-oximes for catalytic α-alkylation of ketones and synthesis of 2-substituted quinolines

Halder, Supriyo; Naskar, Srijita; Jana, Debashis; Kanrar, Gopal; Pramanik, Kausikisankar; Ganguly, Sanjib

doi:10.1039/d4nj00391h

New J. Chem.

2024

DOI: 10.1039/d4nj00391h

|View full text |Cite

Ruthenium complexes of redox non-innocent aryl-azo-oximes for catalytic α-alkylation of ketones and synthesis of 2-substituted quinolines

Supriyo Halder,

Srijita Naskar,

Debashis Jana

et al.

Abstract: Ruthenium(II) complexes [RuL(CO)Cl(PPh3)2], 1a – 4a have been synthesized with ligands PhN=NC(Ar)NOH, HL 1 ‒ 4 respectively by varying the pendant aryl (Ar) groups. The molecular geometries all four complexes...

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

References 89 publications

(108 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

Dehydrogenative Coupling for Synthesis of Quinazolin‐4(3H)‐ones via Tandem Reaction using Ruthenium(II)‐Phenyl‐Azo‐Naphthaldoxime: An Experimental and Theoretical Investigation

Halder,

Naskar,

Jana

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

The bidentate N, N, donor phenyl‐azo‐naphthaldoxime NpLH, 1 was used to synthesize the ruthenium(II) complex trans‐[Ru(NpL)(CO)Cl(PPh3)2], 2. It has been characterized by SCXRD, electrochemical and spectral studies. Computational analysis indicates that the low‐lying p*‐LUMO of the complex has substantial azo‐character of coordinated ligand. This property has been exploited to form an efficient electron transfer pre‐catalyst to effectuate dehydrogenative functionalization of a large number of benzyl alcohols to quinazolin‐4(3H)‐ones via condensation with diverse o‐amino benzamides as well as N‐substituted benzamides under aerobic conditions (57 entries). A reaction mechanism has been projected via isolation of intermediates and certain control experiments. Furthermore, it has been substantiated by theoretical scrutiny using density functional theory (DFT) calculation. The catalytic cycle involves stepwise hydrogen atom transfer (HAT) from benzyl alcohols to the Nazo atoms of the coordinated ligand with subsequent removal of the H‐atoms from the Nazo atoms to regenerate the active catalyst.

show abstract

Dehydrogenative Coupling for Synthesis of Quinazolin‐4(3H)‐ones via Tandem Reaction using Ruthenium(II)‐Phenyl‐Azo‐Naphthaldoxime: An Experimental and Theoretical Investigation

Halder,

Naskar,

Jana

et al. 2024

Chemistry An Asian Journal

View full text Add to dashboard Cite

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Ruthenium complexes of redox non-innocent aryl-azo-oximes for catalytic α-alkylation of ketones and synthesis of 2-substituted quinolines

Abstract: Ruthenium(II) complexes [RuL(CO)Cl(PPh3)2], 1a – 4a have been synthesized with ligands PhN=NC(Ar)NOH, HL 1 ‒ 4 respectively by varying the pendant aryl (Ar) groups. The molecular geometries all four complexes...

Cited by 1 publication

References 89 publications

Dehydrogenative Coupling for Synthesis of Quinazolin‐4(3H)‐ones via Tandem Reaction using Ruthenium(II)‐Phenyl‐Azo‐Naphthaldoxime: An Experimental and Theoretical Investigation

Dehydrogenative Coupling for Synthesis of Quinazolin‐4(3H)‐ones via Tandem Reaction using Ruthenium(II)‐Phenyl‐Azo‐Naphthaldoxime: An Experimental and Theoretical Investigation

Contact Info

Product

Resources

About