Metal -free PhI(OAc)<sub>2</sub>-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

Gao, Tianyong; Yang, Y.B.; Hu, Liangzhen; Luo, Dan; Zhang, Mengjie; Xiong, Yan

doi:10.1039/d2ob02281h

Org. Biomol. Chem.

2023

DOI: 10.1039/d2ob02281h

|View full text |Cite

Metal -free PhI(OAc)₂-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

Tianyong Gao¹,

Y.B. Yang²,

Liangzhen Hu³

et al.

Abstract: A metal-free oxidative decarboxylation reaction of propiolic acids mediated by hypervalent iodine(III) reagents was described. This decarboxylative C–O bond-forming reaction used a combination of (diacetoxyiodo)benzene and aromatic, heteroaromatic or aliphatic...

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 68 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

Yu,

Li,

et al. 2024

Catalysts

View full text Add to dashboard Cite

An efficient and operationally simple method for the synthesis of α-acyloxy ketones through the readily available 2-methylimidazole-promoted reaction of α-hydroxy ketones and anhydrides is developed. In the reaction, the anhydrides act as both a substrate and a solvent. The new method features good substrate tolerance, mild reaction conditions, readily accessible starting materials, and excellent yields, providing facile and green access to the targets. Importantly, the reaction also avoids the use of reagents with pungent odors, such as pyridine, in traditional esterification, which may promote the development of organocatalysis using nitrogen-containing heterocyclic compounds as catalysts.

show abstract

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

Yu,

Li,

et al. 2024

Catalysts

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.

Metal -free PhI(OAc)₂-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

Abstract: A metal-free oxidative decarboxylation reaction of propiolic acids mediated by hypervalent iodine(III) reagents was described. This decarboxylative C–O bond-forming reaction used a combination of (diacetoxyiodo)benzene and aromatic, heteroaromatic or aliphatic...

Cited by 1 publication

References 68 publications

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

Contact Info

Product

Resources

About

Metal -free PhI(OAc)2-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations

Abstract: A metal-free oxidative decarboxylation reaction of propiolic acids mediated by hypervalent iodine(III) reagents was described. This decarboxylative C–O bond-forming reaction used a combination of (diacetoxyiodo)benzene and aromatic, heteroaromatic or aliphatic...

Cited by 1 publication

References 68 publications

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

A Novel 2-Methylimidazole Promoted Oxyacyloxylation of α-Hydroxy Ketones and Anhydrides: An Easy Access to α-Acyloxy Ketones

Contact Info

Product

Resources

About

Metal -free PhI(OAc)₂-oxidized decarboxylation of propiolic acids towards synthesis of α-acetoxy ketones and insights into general decarboxylation with DFT calculations