Multicomponent Reactions Among Alkyl Isocyanides, sp Reactants, and sp2
           Carbon Cages

Li, Yanbang; Kopcha, William P.; Rodríguez‐Fortea, Antonio; Zhang, Jianyuan

doi:10.1055/a-1741-9000

Cited by 5 publications

(2 citation statements)

References 87 publications

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“…The reaction among isocyanides, alkynes and fullerenes was reviewed by Li et al [91][92][93] Investigating the types of alkynes in this type of multicomponent reaction requires a more detailed investigation to discover a way to carry out the reaction of alkynes that are not involved in the reaction. Even checking the position of C-H alkynes and activating this part to be involved in the reaction need to be investigated.…”

Section: Reaction Of Isocyanidesmentioning

confidence: 99%

Recent advances in the application of alkynes in multicomponent reactions

Hosseininezhad,

Ramazani

2024

RSC Adv.

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Section: Reaction Of Isocyanidesmentioning

confidence: 99%

Recent advances in the application of alkynes in multicomponent reactions

Hosseininezhad,

Ramazani

2024

RSC Adv.

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“…It is worth noting that the cluster motion in crystals of 4 has been slowed down, but not in 2a , due to the close interaction with the exohedral organic appendant of a neighboring molecule as supported by DFT calculations. In addition, allenes linked to ester group(s), which are also sp ‐hybridized, have been taken into consideration, [ 12 ] but similar multi‐component reactions suffered from low conversion and poor selectivity. Notably, similar reactions [ 13 ] have been applied to C 60 , leading to selective formation of cyclo‐adducts for internal alkyne and allene substrates, but no isolable products for terminal alkyne substrates.…”

Section: Mono‐addition Of Emfsmentioning

confidence: 99%

Advances in Regioselective Functionalization of Endohedral Metallofullerenes^†

Sun

Kopcha

et al. 2023

Chin. J. Chem.

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Comprehensive Summary Endohedral metallofullerenes (EMFs) are a family of molecules with metal clusters or ions encapsulated inside a fullerene cage. Their unique structures provide a powerful interface for organic chemists to manipulate metal elements. Over a decade ago, many reactions on empty fullerenes were adopted for EMFs, resulting in a series of reactions that are well‐established and reviewed in the literature. In recent years, new topics have emerged in EMF chemistry. First, new addition reactions were developed, notably some that are not based on known empty‐fullerene reactions. Second, considerable progress has been made on regioselective multi‐additions on EMFs. Finally, EMFs have been covalently conjugated with fullerene C60 to form functional materials. This Recent Advances article will focus on these new developments and discuss their implication for future directions of EMFs.

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Dearomative Ring‐Fused Azafulleroids and Carbazole‐Derived Metallofullerenes: Reactivity Dictated by Encapsulation in a Fullerene Cage

Liu,

Wang,

Xia

et al. 2023

Angewandte Chemie

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Herein, we report divergent additions of 2,2′‐diazidobiphenyls to C60 and Sc3N@Ih‐C80. In stark contrast to that of the previously reported bis‐azide additions, the unexpected cascade reaction leads to the dearomative formation of azafulleroids 2 fused with a 7‐6‐5‐membered ring system in the case of C60. In contrast, the corresponding reaction with Sc3N@Ih‐C80 switches to the C−H insertion pathway, thereby resulting in multiple isomers, including a carbazole‐derived [6,6]‐azametallofulleroid 3 and a [5,6]‐azametallofulleroid 4 and an unusual 1,2,3,6‐tetrahydropyrrolo[3,2‐c]carbazole‐derived metallofullerene 5, whose molecular structures have been unambiguously determined by single‐crystal X‐ray diffraction analyses. Among them, the addition type of 5 is observed for the first time in all reported additions of azides to fullerenes. Furthermore, unexpected isomerizations from 3 to 5 and from 4 to 5 have been discovered, providing the first examples of the isomerization of an azafulleroid to a carbazole‐derived fullerene rather than an aziridinofullerene. In particular, the isomerism of the [5,6]‐isomer 4 to the [5,6]‐isomer 5 is unprecedented in fullerene chemistry, contradicting the present understanding that isomerization generally occurs between [5,6]‐ and [6,6]‐isomers. Control experiments have been carried out to rationalize the reaction mechanism. Furthermore, representative azafulleroids have been applied in organic solar cells, thereby resulting in improved power conversion efficiencies.

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Multicomponent Reactions Among Alkyl Isocyanides, sp Reactants, and sp2 Carbon Cages

Cited by 5 publications

References 87 publications

Recent advances in the application of alkynes in multicomponent reactions

Recent advances in the application of alkynes in multicomponent reactions

Advances in Regioselective Functionalization of Endohedral Metallofullerenes^†

Dearomative Ring‐Fused Azafulleroids and Carbazole‐Derived Metallofullerenes: Reactivity Dictated by Encapsulation in a Fullerene Cage

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Multicomponent Reactions Among Alkyl Isocyanides, sp Reactants, and sp2 Carbon Cages

Cited by 5 publications

References 87 publications

Recent advances in the application of alkynes in multicomponent reactions

Recent advances in the application of alkynes in multicomponent reactions

Advances in Regioselective Functionalization of Endohedral Metallofullerenes†

Dearomative Ring‐Fused Azafulleroids and Carbazole‐Derived Metallofullerenes: Reactivity Dictated by Encapsulation in a Fullerene Cage

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Advances in Regioselective Functionalization of Endohedral Metallofullerenes^†