Overcrowded Triply Fused Carbo[7]helicene

This paper presents the synthesis and comprehensive analysis of a highly contorted and doubly negatively curved multihelicene compound, composed of three carbo[7]­helicene units fused within a central six-membered ring. The synthesis of this compound involved a [2 + 2 + 2] cycloaddition reaction of...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2023-07, Vol.145 (28), p.15084-15087
Main Authors: Artigas, Albert, Rigoulet, Florian, Giorgi, Michel, Hagebaum-Reignier, Denis, Carissan, Yannick, Coquerel, Yoann
Format: Article
Language:English
Subjects:
catalysts
Chemical Sciences
cycloaddition reactions
helicenes
magnetism
Organic chemistry
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Summary:This paper presents the synthesis and comprehensive analysis of a highly contorted and doubly negatively curved multihelicene compound, composed of three carbo[7]­helicene units fused within a central six-membered ring. The synthesis of this compound involved a [2 + 2 + 2] cycloaddition reaction of 13,14-picyne, employing a Ni(0) catalyst, which exhibited superior performance compared to conventional Pd(0) catalysts. The evaluation of aromaticity in this triple carbo[7]­helicene, utilizing magnetic and electronic criteria, led to noteworthy insights challenging the limitations of Clar’s model of aromaticity.
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c05415