Bipyrrole boomerangs via Pd-mediated tandem cyclization-oxygenation. Controlling reaction selectivity and electronic properties - Archive ouverte HAL Access content directly
Journal Articles Beilstein Journal of Organic Chemistry Year : 2020

Bipyrrole boomerangs via Pd-mediated tandem cyclization-oxygenation. Controlling reaction selectivity and electronic properties

Abstract

Boomerang-shaped bipyrroles containing donor-acceptor units were obtained through a tandem palladium-mediated reaction consisting of a cyclization step, involving double C-H bond activation, and a double alpha-oxygenation. The latter reaction can be partly suppressed for the least reactive systems, providing access to alpha-unsubstituted boomerangs for the first time. These "alpha-free" systems are highly efficient fluorophores, with emission quantum yields exceeding 80% in toluene. Preliminary measurements show that helicene-like boomerangs may be usable as circularly polarized luminescent materials.
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Dates and versions

hal-02797043 , version 1 (05-06-2020)

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Attribution - CC BY 4.0

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Liliia Moshniaha, Marika Zyia-Karwowska, Joanna Cybinska, Piotr J. Chmielewski, Ludovic Favereau, et al.. Bipyrrole boomerangs via Pd-mediated tandem cyclization-oxygenation. Controlling reaction selectivity and electronic properties. Beilstein Journal of Organic Chemistry, 2020, 16, pp.895-903. ⟨10.3762/bjoc.16.81⟩. ⟨hal-02797043⟩
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