Fullerene-Cation-Mediated Noble-Metal-Free Direct Introduction of Functionalized Aryl Groups onto [60]Fullerene

Organic Letters
Xiao-Yu YangYutaka Matsuo

Abstract

Aryl[60]fullerenyl cations (ArC60+), which were generated by heating aryl[60]fullerenyl dimers (ArC60-C60Ar) to generate aryl[60]fullerenyl radicals (ArC60•) followed by oxidation using Cu(II) salts (Cu(BF4)2(aq)), were reacted with various functionalized aryl boronic acids to produce functionalized 1,4-diaryl[60]fullerenes. This protocol tolerated various functional groups, such as OH, NH2, COCH3, and Cl substituents, with yields reaching 93%. C60Ar1Ar2 (Ar2 = p-NH2C6H4) was used as a dopant in a photoactive CH3NH3PbI3 layer of a perovskite solar cell.

References

Mar 2, 2002·The Journal of Organic Chemistry·Yusuke Tajima, Kazuo Takeuchi
Nov 19, 2003·Accounts of Chemical Research·Eiichi Nakamura, Hiroyuki Isobe
Jul 14, 2006·Organic Letters·Yusuke TajimaKazuo Takeuchi
Jul 27, 2006·Journal of the American Chemical Society·Yutaka MatsuoEiichi Nakamura
Dec 15, 2006·Chemical Reviews·Carlo Thilgen, François Diederich
Dec 15, 2006·Chemical Reviews·Francesco Giacalone, Nazario Martín
Mar 28, 2007·Angewandte Chemie·Akihiko IwashitaEiichi Nakamura
Jun 15, 2007·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
Jul 26, 2008·Chemical Reviews·Yutaka Matsuo, Eiichi Nakamura
Feb 21, 2009·Chemistry : a European Journal·Masakazu Nambo, Kenichiro Itami
Mar 7, 2009·Organic Letters·Guan-Wu WangZhong-Xiu Chen
Jul 10, 2009·Chemical Society Reviews·Dirk M GuldiNazario Martín
Feb 10, 2011·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
Jul 16, 2013·Chemistry, an Asian Journal·Yongfang Li
Feb 19, 2014·Journal of the American Chemical Society·Yoko AbeEiichi Nakamura

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