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[2,3]-Sigmatropic rearrangement with [1.1.1]propellane

Suparnak Midya, Aksar Ali and Durga Prasad Hari ()
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Suparnak Midya: Indian Institute of Science
Aksar Ali: Indian Institute of Science
Durga Prasad Hari: Indian Institute of Science

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract The most established reactivity of [1.1.1]propellane involves addition reactions at the bridge C-C bond, resulting in the formation of bicyclo[1.1.1]pentane derivatives. Herein, we present a [2,3]-sigmatropic rearrangement that uses [1.1.1]propellane as a carbene precursor to rapidly access allenylated or allylated methylenecyclobutanes. The reaction is highly efficient and scalable, works well under mild conditions, and can tolerate a diverse range of functional groups on propargyl and allyl sulfides/selenides. Another significant achievement of this approach is the utility of the obtained products in synthesizing substituted bicyclo[2.1.1]hexanes, potential bioisosteres of ortho and meta-substituted benzenes, by developing a photocatalyzed radical cascade cyclization. Density functional theory calculations suggest the involvement of a copper-bound five-membered transition state.

Date: 2025
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DOI: 10.1038/s41467-025-60805-2

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