Palladium-Catalyzed Cyclization: Regioselectivity and Structure of Arene-Fused C60 Derivatives

Journal of the American Chemical Society
Yoshifumi HashikawaYasujiro Murata

Abstract

The palladium-catalyzed cyclization on the fullerene C60 cage has been achieved using several aryl halides and C60. This reaction was found to be accelerated by the addition of pivalic acid, which can be rationally explained by the computational study based on the concerted metalation-deprotonation mechanism. We also demonstrated the regioselective π-functionalization using prefunctionalized designed molecules possessing the same substructure on the C60 cage. The single crystal X-ray analysis and electrostatic potential map revealed that the orientation of entrapped H2O inside the naphthalene-fused open-cage C60 derivative is electrostatically demanded due to the naphthalene-fusion and construction of the opening.

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Citations

Nov 20, 2018·Chemical Communications : Chem Comm·Yoshifumi HashikawaYasujiro Murata
Dec 6, 2018·Chemistry : a European Journal·Yoshifumi Hashikawa, Yasujiro Murata
Aug 12, 2020·Chemical Communications : Chem Comm·Sally BloodworthRichard J Whitby
Dec 2, 2020·Chemistry : a European Journal·Yoshifumi HashikawaYasujiro Murata
Apr 10, 2021·Chemistry : a European Journal·Yoshifumi HashikawaYasujiro Murata
Apr 3, 2021·Chemistry : a European Journal·Yoshifumi HashikawaYasujiro Murata
Mar 3, 2018·The Journal of Organic Chemistry·Kazutaka ShoyamaFrank Würthner
Jul 26, 2019·Journal of the American Chemical Society·Yoshifumi Hashikawa, Yasujiro Murata
Dec 3, 2021·Organic Letters·Yoshifumi HashikawaYasujiro Murata
Jan 15, 2022·Organic & Biomolecular Chemistry·Yoshifumi Hashikawa, Yasujiro Murata

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