Phosphine-catalysed [3 + 2] cycloadditions of buta-2,3-dienoates with [60]fullerene

Shu, Le; Sun, Wei-Quan; Zhang, Dan‐Wei; Wu, Shuisheng; Wu, Hou‐Ming; Xu, Jing-Fei; Lao, Xia-Fei

doi:10.1039/a605923f

Cited by 50 publications

(4 citation statements)

References 6 publications

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“…Finally, buta-2,3-dienoates and buta-2-ynoates, in the presence of phosphine as catalyst, have been found to react with C 60 in a [3+2] fashion [83,84], contrary to the earlier observations of yielding [2+2] cycloadducts [85]. …”

Section: [3+2] Cycloadditionscontrasting

confidence: 51%

Organofullerene Materials

Tagmatarchis

Prato

2004

Fullerene-Based Materials

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Section: [3+2] Cycloadditionscontrasting

confidence: 51%

Organofullerene Materials

Tagmatarchis

Prato

2004

Fullerene-Based Materials

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“…Likewise, annulation products can also be obtained when using [60]fullerene as an electrophile in the [3 + 2] annulation (Scheme 189). Wu 256 and Kroto 257 independently demonstrated a way to generate derivatized [60]fullerenes from reactions with 2,3-butadienoates in the presence of tributylphosphine. Increasing the reaction temperature and switching the catalyst to triphenylphosphine allowed isolation of the annulation products in higher yields.…”

Section: Nucleophilic Phosphine Catalysis Of Allenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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“…The new [3 + 2] reaction exhibits a wide range of applications in organic synthesis, e.g., the synthesis of [60]fullerene cycloadducts, l -glutamate analogues ( 75 ), and pentabromopseudilin ( 76 ) (Scheme ) 38 …”

Section: [3 + 2] Cycloaddtion Of Substituted 2-alkynoatesmentioning

confidence: 99%

Reactions of Electron-Deficient Alkynes and Allenes under Phosphine Catalysis

2001

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The development of some new synthetic reactions derived from nucleophilic addition of phosphines to electron-deficient carbon-carbon triple bonds is described. These reactions show that the phosphine plays the role of a nucleophile as well as an excellent leaving group. The central problem is to generate a 1,3-dipole from alkynoates or allenoates (2,3-butadienoates) by interaction with various phosphines. This study illuminates the unusual phenomena and shows how this understanding allows control of the reaction.

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Phosphine-catalysed [3 + 2] cycloadditions of buta-2,3-dienoates with [60]fullerene

Abstract: Fullerene reacts with buta-2,3-dienoates in the presence of phosphine to form alkyl 3AH-1,2-([1A,2A]cyclopenta)-[60]fullerene-5A-carboxylates.

Cited by 50 publications

References 6 publications

Organofullerene Materials

Organofullerene Materials

Phosphine Organocatalysis

Reactions of Electron-Deficient Alkynes and Allenes under Phosphine Catalysis

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