Palladium-Catalyzed Heteroannulation of [60]Fullerene with Anilides via C−H Bond Activation

Zhu, Bo; Wang, Guan‐Wu

doi:10.1021/ol901675t

Cited by 114 publications

(35 citation statements)

References 60 publications

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“…[46] Chuang, Wang, and co-workers reported the palladium-catalyzed synthesis of fulleroisoquinolinones by the annulation of C 60 with N-alkyl benzamides through CÀH activation (Scheme 45, bottom). The annulation reactions of fullerene with anilides and N-alkyl benzamides through a C À C/C À N bond-formation sequence were reported by Zhu and Wang and by Chuang et al, respectively.…”

Section: Annulation Of Amides With Arenesmentioning

confidence: 99%

“…Zhu and Wang accomplished the synthesis of a wide variety of fulleroindolines in a highly regioselective manner through the palladium-catalyzed annulation of C 60 with anilides, thereby demonstrating the first example of exploiting the C À H activation strategy to functionalize fullerenes (Scheme 45, top). [46] Chuang, Wang, and co-workers reported the palladium-catalyzed synthesis of fulleroisoquinolinones by the annulation of C 60 with N-alkyl benzamides through CÀH activation (Scheme 45, bottom). [47] Trifluoroacetic acid was used as a key co-solvent for improving the reaction performance.…”

Section: Annulation Of Amides With Arenesmentioning

confidence: 99%

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Amide‐Directed Tandem CC/CN Bond Formation through CH Activation

Zhu

Wang

Falck

2012

Chemistry An Asian Journal

270

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The transformation of C-H bonds into other chemical bonds is of great significance in synthetic chemistry. C-H bond-activation processes provide a straightforward and atom-economic strategy for the construction of complex structures; as such, they have attracted widespread interest over the past decade. As a prevalent directing group in the field of C-H activation, the amide group not only offers excellent regiodirecting ability, but is also a potential C-N bond precursor. As a consequence, a variety of nitrogen-containing heterocycles have been obtained by using these reactions. This Focus Review addresses the recent research into the amide-directed tandem C-C/C-N bond-formation process through C-H activation. The large body of research in this field over the past three years has established it as one of the most-important topics in organic chemistry.

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Section: Annulation Of Amides With Arenesmentioning

confidence: 99%

Section: Annulation Of Amides With Arenesmentioning

confidence: 99%

Amide‐Directed Tandem CC/CN Bond Formation through CH Activation

Zhu

Wang

Falck

2012

Chemistry An Asian Journal

270

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“…The employed [60]fulleroindoline 1 (for structure see Scheme 1) was synthesized accorrding to our previous procedure. [9] The cyclic voltammogram (CV) of 1 in o-dichlorobenzene (ODCB; Figure 2 a) shows that the first redox is a reversible one-electron transfer process with an E 1/2 of À0.56 V versus a saturated calomel electrode, whereas the second redox is chemically irreversible on the CV timescale, as evidenced by the appearance of decreased anodic current in the reverse scan. [5c, 10, 11] This result indicates that a heterolytic cleavage of the C 60 À N bond likely occurs after 1 accepts two electrons (Scheme 1).…”

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confidence: 99%

Regioselective Electrosynthesis of Rare 1,2,3,16‐Functionalized [60]Fullerene Derivatives

et al. 2014

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Fullerene derivatives with different addition patterns exhibit different physical, chemical, and biological properties, which are important for fullerene applications. Novel and rare 1,2,3,16-functionalized [60]fullerene derivatives having a five-membered heterocycle fused to a [5,6]-junction were obtained with high regioselectivity by electrochemical derivatization of a [60]fulleroindoline. The product structures were determined by spectroscopic data and single-crystal X-ray analysis. The obtained high regioselectivity was rationalized using theoretical calculations.

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“…Palladium acetate catalyzes cycloaddition onto C 60 of a variety of anilides through a C-H bond activation, affording fulleroindolines (14) in a highly regioselective manner (Scheme 5) [39].…”

Section: New Reactions On Fullerenes Involving Metalsmentioning

confidence: 99%

Buckyballs

Delgado

Filippone

Giacalone

et al. 2013

Topics in Current Chemistry

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Buckyballs represent a new and fascinating molecular allotropic form of carbon that has received a lot of attention by the chemical community during the last two decades. The unabating interest on this singular family of highly strained carbon spheres has allowed the establishing of the fundamental chemical reactivity of these carbon cages and, therefore, a huge variety of fullerene derivatives involving [60] and [70]fullerenes, higher fullerenes, and endohedral fullerenes have been prepared. Much less is known, however, of the chemistry of the uncommon non-IPR fullerenes which currently represent a scientific curiosity and which could pave the way to a range of new fullerenes. In this review on buckyballs we have mainly focused on the most recent and novel covalent chemistry of fullerenes involving metal catalysis and asymmetric synthesis, as well as on some of the most significant advances in supramolecular chemistry, namely H-bonded fullerene assemblies and the search for efficient concave receptors for the convex surface of fullerenes. Furthermore, we have also described the recent advances in the macromolecular chemistry of fullerenes, that is, those polymer molecules endowed with fullerenes which have been classified according to their chemical structures. This review is completed with the study of endohedral fullerenes, a new family of fullerenes in which the carbon cage of the fullerene contains a metal, molecule, or metal complex in the inner cavity. The presence of these species affords new fullerenes with completely different properties and chemical reactivity, thus opening a new avenue in which a more precise control of the photophysical and redox properties of fullerenes is possible. The use of fullerenes for organic electronics, namely in photovoltaic applications and molecular wires, complements the study and highlights the interest in these carbon allotropes for realistic practical applications. We have pointed out the so-called non-IPR fullerenes - those that do not follow the isolated pentagon rule - as the most intriguing class of fullerenes which, up to now, have only shown the tip of the huge iceberg behind the examples reported in the literature. The number of possible non-IPR carbon cages is almost infinite and the near future will show us whether they will become a reality.

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Palladium-Catalyzed Heteroannulation of [60]Fullerene with Anilides via C−H Bond Activation

Abstract: The palladium-catalyzed reaction of [60]fullerene with a variety of readily available anilides, initiated by C-H bond activation and followed by cyclization, afforded [60]fulleroindolines in a highly regioselective manner. A plausible reaction mechanism was proposed.

Cited by 114 publications

References 60 publications

Amide‐Directed Tandem CC/CN Bond Formation through CH Activation

Amide‐Directed Tandem CC/CN Bond Formation through CH Activation

Regioselective Electrosynthesis of Rare 1,2,3,16‐Functionalized [60]Fullerene Derivatives

Buckyballs

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