Regioselective unsymmetrical tetraallylation of C(60) through palladium catalysis

Journal of the American Chemical Society
Masakazu NamboKenichiro Itami

Abstract

A Pd-catalyzed tetraallylation of C(60) that selectively occurs with an unsymmetrical addition pattern has been established. Treatment of C(60) with CH(2)=CHCH(2)Cl, CH(2)=CHCH(2)SnBu(3), and PdCl(2)[P(OPh)(3)](2) in 1,2-Cl(2)C(6)H(4) at 50 degrees C afforded the tetraallylated fullerene in 74% yield with virtually complete regioselectivity. Mechanistic investigations showed that (i) tetraallylation proceeds through consecutive nucleophilic/electrophilic allylations [likely via a bis(pi-allyl)palladium intermediate] and (ii) both steric (for the first diallylation) and electronic (for the second diallylation) factors are responsible for the high regioselectivity.

References

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Apr 12, 2003·The Journal of Organic Chemistry·Zhongwen Wang, Mark S Meier
Jun 4, 2004·Journal of the American Chemical Society·Niclas SolinKálmán J Szabó
Dec 15, 2006·Chemical Reviews·Carlo Thilgen, François Diederich
Jun 15, 2007·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
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Feb 21, 2009·Chemistry : a European Journal·Masakazu Nambo, Kenichiro Itami

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Citations

Jul 13, 2011·Journal of the American Chemical Society·Shirong LuYoshinori Yamamoto
Apr 21, 2012·Organic Letters·Wei-Wei ChangXiang Gao
Mar 15, 2015·Chemical Communications : Chem Comm·Weili SiTienan Jin
Sep 8, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Kenichiro Itami
Sep 28, 2017·Organic & Biomolecular Chemistry·Michio YamadaYutaka Maeda
Jun 5, 2010·The Journal of Organic Chemistry·Dazhi YangLiangbing Gan
Oct 6, 2010·Organic Letters·Wallace W H WongAndrew B Holmes
Feb 10, 2011·Journal of the American Chemical Society·Masakazu NamboKenichiro Itami
Feb 24, 2011·The Journal of Organic Chemistry·Shih-Ching ChuangGuan-Wu Wang

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