Issue 74, 2019

Intramolecular benzoallene–alkyne cycloaddition initiated by site-selective SN2′ reaction of epoxytetracene en route to π-extended pyracylene

Abstract

A hydrogen halide promoted cascade reaction of epoxytetracene to afford halo-benzoindenotetracene including a benzoallene intermediate was developed. The remaining two alkynyl groups in benzoindenotetracene were further reacted with norbornadiene or arylamine through transition metal-catalyzed cyclization to give π-extended pyracylene derivatives.

Graphical abstract: Intramolecular benzoallene–alkyne cycloaddition initiated by site-selective SN2′ reaction of epoxytetracene en route to π-extended pyracylene

Supplementary files

Article information

Article type
Communication
Submitted
17 Jul 2019
Accepted
23 Aug 2019
First published
24 Aug 2019

Chem. Commun., 2019,55, 11021-11024

Author version available

Intramolecular benzoallene–alkyne cycloaddition initiated by site-selective SN2′ reaction of epoxytetracene en route to π-extended pyracylene

K. Kitamura, K. Asahina, K. Adachi and T. Hamura, Chem. Commun., 2019, 55, 11021 DOI: 10.1039/C9CC05500B

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