Cleavage of the Inert C(sp2)–Ar σ‑Bond of Alkenes by a Spatial Constrained Interaction with Phosphinidene

Cleavage of the Inert C(sp2)–Ar σ‑Bond of Alkenes by a Spatial Constrained Interaction with Phosphinidene

[1 + 2] cycloaddition is a classical reaction between the electrophilic phosphinidene and an alkene. However, a spatial constraint blocks this well-known reaction and enables an unprecedented chemoselective C­(sp2)–Ar σ-bond insertion of the alkene. The theoretical calculations demonstrate that this...

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Veröffentlicht in:Journal of the American Chemical Society 2020-12, Vol.142 (50), p.20973-20978
Hauptverfasser: Wang, Junjian, Wei, Donghui, Duan, Zheng, Mathey, François
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creator Wang, Junjian
Wei, Donghui
Duan, Zheng
Mathey, François
description [1 + 2] cycloaddition is a classical reaction between the electrophilic phosphinidene and an alkene. However, a spatial constraint blocks this well-known reaction and enables an unprecedented chemoselective C­(sp2)–Ar σ-bond insertion of the alkene. The theoretical calculations demonstrate that this C–C bond cleavage is energetically feasible and thermodynamically favored through an electrophilic rearrangement and concomitant 1,9-aryl migration without involving any strained intermediate.
doi_str_mv 10.1021/jacs.0c11195
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title Cleavage of the Inert C(sp2)–Ar σ‑Bond of Alkenes by a Spatial Constrained Interaction with Phosphinidene
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