Palladium-catalyzed three-component 1,4-aminoarylation of [60]fullerene with aryl iodides and <i>N</i>-methoxysulfonamides, and further transformations

Comprehensive SummaryA series of unreported fullerodihydropyridine‐3‐ones were synthesized as a new family of fullerene derivatives in moderate to good yields by a simple one‐step reaction of [60]fullerene with cheap and readily available β‐substituted ethylamines in the absence or presence of arylacetaldehydes under the assistance of Cu(OAc)2. The in situ generation of arylacetaldehydes by the C—N bond cleavage of arylethylamines avoided their complex synthesis in advance and realized the preparation of fullerodihydropyridine‐3‐ones with structural and functional diversities, which may have promising applications in perovskite solar cells to improve the performance of photovoltaic devices due to the existence of a large π‐conjugated system on the dihydropyridine‐3‐one ring.

show abstract

Cu(OAc)₂‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes^†

Liu

Wang

et al. 2023

Chin. J. Chem.

View full text Add to dashboard Cite

show abstract

Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction^†

Liu

Yang

et al. 2023

Chin. J. Chem.

View full text Add to dashboard Cite

Comprehensive Summary Chemical functionalization of fullerenes has been an important topic in fullerene chemistry. Herein, an unprecedented Pd‐catalyzed migration reaction of [60]fullerene with allyloxy‐tethered aryl iodides is present for the preparation of novel [60]fullerene‐fused allylbenzofurans. The use of 1,2‐bis(diphenylphosphino)benzene (DPPBz) as a ligand is crucial for the success of the transformation. The reaction shows high chemo‐ and regioselectivity, and is flexible with regard to allyl‐migration site, providing a new and efficient approach to rare [60]fullerene‐fused benzofurans. Control experiments disclose that the reaction most probably undergoes a sequential C—O bond cleavage/allyl‐migration/intermolecular cycloaddition cascade process.

show abstract

Synthesis of Diverse 1,4‐(Azaindole)[60]fullerenes via Transition‐Metal Free Three‐Component Coupling Reaction of Azaindoles, C₆₀, and Bromoalkanes/Triphenylamines^†

et al. 2023

View full text Add to dashboard Cite

Comprehensive SummaryA transition‐metal free three‐component coupling reaction of azaindoles, C60, and bromoalkanes/triphenylamines has been developed to provide an efficient access to diverse azaindole functionalized 1,4‐C60 adducts. This protocol exhibits low cost, operational simplicity, wide substrate scope, and mild and convenient conditions.This article is protected by copyright. All rights reserved.

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.

Palladium-catalyzed three-component 1,4-aminoarylation of [60]fullerene with aryl iodides and N-methoxysulfonamides, and further transformations

Cited by 9 publications

References 68 publications

Cu(OAc)₂‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes^†

Cu(OAc)₂‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes^†

Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction^†

Synthesis of Diverse 1,4‐(Azaindole)[60]fullerenes via Transition‐Metal Free Three‐Component Coupling Reaction of Azaindoles, C₆₀, and Bromoalkanes/Triphenylamines^†

Contact Info

Product

Resources

About

Palladium-catalyzed three-component 1,4-aminoarylation of [60]fullerene with aryl iodides and N-methoxysulfonamides, and further transformations

Cited by 9 publications

References 68 publications

Cu(OAc)2‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes†

Cu(OAc)2‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes†

Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction†

Synthesis of Diverse 1,4‐(Azaindole)[60]fullerenes via Transition‐Metal Free Three‐Component Coupling Reaction of Azaindoles, C60, and Bromoalkanes/Triphenylamines†

Contact Info

Product

Resources

About

Cu(OAc)₂‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes^†

Cu(OAc)₂‐Mediated Synthesis of Fullerodihydropyridine‐3‐ones via the Reaction of [60]Fullerene with β‐Substituted Ethylamines in the Absence or Presence of Arylacetaldehydes^†

Synthesis of [60]Fullerene‐Fused Allylbenzofurans via Palladium‐Catalyzed Migration Reaction^†

Synthesis of Diverse 1,4‐(Azaindole)[60]fullerenes via Transition‐Metal Free Three‐Component Coupling Reaction of Azaindoles, C₆₀, and Bromoalkanes/Triphenylamines^†