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Functionalization of [60]Fullerene via Palladium-Catalyzed C–H Bond Activation

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C-H Bond Activation and Catalytic Functionalization I

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 55))

Abstract

The palladium-catalyzed C–H bond activation strategy has been successfully applied to fullerene chemistry, and several types of [60]fullerene-fused heterocycles and carbocycles have been obtained. The synthesis of [60]fullerene-fused indolines, isoquinolinones, azepines, tetrahydroisoquinolines, tetrahydrobenzazepines, sultones, tetrahydrobenzooxepines/isochromans, and dihydrophenanthrenes has been achieved by the palladium-catalyzed reactions of [60]fullerene with anilides, benzamides, N-sulfonyl-2-aminobiaryls, N-benzyl sulfonamides, N-(2-arylethyl) sulfonamides, arylsulfonic acids, 2-phenylethyl/benzyl alcohols, and 2-arylbenzoic acids, respectively.

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Abbreviations

BQ:

p-Benzoquinone

Bs:

Benzenesulfonyl

Cs:

4-Chlorobenzenesulfonyl

equiv.:

Equivalent(s)

Et:

Ethyl

h:

Hour(s)

Me:

Methyl

MeCN:

Acetonitrile

mL:

Mililiter(s)

mol:

Mole(s)

Ms:

Methanesulfonyl

ODCB:

ortho-Dichlorobenzene

Ph:

Phenyl

Piv:

Pivaloyl

PTSA:

p-Toluenesulfonic acid

rt:

Room temperature

TFA:

Trifluoroacetic acid

Ts:

p-Toluenesulfonyl

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Authors and Affiliations

  1. CAS Key Laboratory of Soft Matter Chemistry, iChEM (Collaborative Innovation Center of Chemistry for Energy Materials), National Laboratory for Physical Sciences at Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026, P. R. China

    Guan-Wu Wang

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  1. Guan-Wu Wang
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Correspondence to Guan-Wu Wang .

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Editors and Affiliations

  1. Université de Rennes, Rennes, France

    Pierre H. Dixneuf

  2. Université de Rennes , Rennes, France

    Henri Doucet

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Wang, GW. (2015). Functionalization of [60]Fullerene via Palladium-Catalyzed C–H Bond Activation. In: Dixneuf, P., Doucet, H. (eds) C-H Bond Activation and Catalytic Functionalization I. Topics in Organometallic Chemistry, vol 55. Springer, Cham. https://doi.org/10.1007/3418_2015_128

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