Bioinspired Palladium‐Catalyzed Intramolecular C(sp<sup>3</sup>)−H Activation for the Collective Synthesis of Proline Natural Products

The C−H functionalization strategy provides access to valuable molecules that previously required convoluted synthetic attempts. Dual C−H unsymmetrical functionalization, with a single bifunctional reagent, is an effective tactic. Propargyl alcohols (PAs), despite containing a reactive C≡C bond, have not been explored as building blocks via oxidative cleavage. Annulations via C−H activation are a versatile and synthetically attractive strategy. We disclose PA as a new bifunctional reagent for unsymmetrical dual C−H functionalization of biphenylamine for regioselectively annulated outcomes. On tuning the conditions, the annulation bifurcated towards an unusual dual oxidative cyclization. This method accommodates a wide range of PAs and showcases late‐stage diversification of some natural products.

show abstract

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Dattatri

Singam

Suresh

et al. 2023

Angewandte Chemie

View full text Add to dashboard Cite

show abstract

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

et al. 2023

View full text Add to dashboard Cite

show abstract

Palladium‐Catalyzed 2‐Aminoacetophenone Oxime Directed β‐sp² and γ‐sp³ C─H Bond Functionalization of Aryl Carboxamides

Sankar,

Gnanasambandam

2024

ChemistrySelect

View full text Add to dashboard Cite

Pd(II)‐catalyzed 2‐aminoacetophenone oxime‐assisted sp2 and sp3 C─H arylation of aryl carboxamides is disclosed. The 2‐aminoacetophenone oxime is an N,N‐bidentate auxiliary that proceeds C─H activation through a six‐membered palladacycle intermediate, and the activation/functionalization on C(sp3)─H bond by the six‐membered ligand palladacycle is novel and achieved. This auxiliary facilitates the subsequent sp3 and sp2 C─H bond activation/functionalization in one step. The optimized protocol enables access to various aryl groups at the β‐sp2‐ and γ‐sp3‐centers of aryl carboxamides. The bidentate auxiliary is easy to synthesize on a gram scale, and we also described deoximination procedure after C─H functionalization.

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.

Bioinspired Palladium‐Catalyzed Intramolecular C(sp³)−H Activation for the Collective Synthesis of Proline Natural Products

Cited by 4 publications

References 101 publications

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Palladium‐Catalyzed 2‐Aminoacetophenone Oxime Directed β‐sp² and γ‐sp³ C─H Bond Functionalization of Aryl Carboxamides

Contact Info

Product

Resources

About

Bioinspired Palladium‐Catalyzed Intramolecular C(sp3)−H Activation for the Collective Synthesis of Proline Natural Products

Cited by 4 publications

References 101 publications

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Propargyl Alcohols as Bifunctional Reagents for Divergent Annulations of Biphenylamines via Dual C−H Functionalization/Dual Oxidative Cyclization

Palladium‐Catalyzed 2‐Aminoacetophenone Oxime Directed β‐sp2 and γ‐sp3 C─H Bond Functionalization of Aryl Carboxamides

Contact Info

Product

Resources

About

Bioinspired Palladium‐Catalyzed Intramolecular C(sp³)−H Activation for the Collective Synthesis of Proline Natural Products

Palladium‐Catalyzed 2‐Aminoacetophenone Oxime Directed β‐sp² and γ‐sp³ C─H Bond Functionalization of Aryl Carboxamides