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Article Dans Une Revue Angewandte Chemie International Edition Année : 2019

Photochemical Strain‐Release‐Driven Cyclobutylation of C(sp 3 )‐Centered Radicals

Résumé

Abstract A new photoredox‐catalyzed decarboxylative radical addition approach to functionalized cyclobutanes is described. The reaction involves an unprecedented formal Giese‐type addition of C(sp 3 )‐centered radicals to highly strained bicyclo[1.1.0]butanes. The mild photoredox conditions, which make use of a readily available and bench stable phenyl sulfonyl bicyclo[1.1.0]butane, proved to be amenable to a diverse range of α‐amino and α‐oxy carboxylic acids, providing a concise route to 1,3‐disubstituted cyclobutanes. Furthermore, kinetic studies and DFT calculations unveiled mechanistic details on bicyclo[1.1.0]butane reactivity relative to the corresponding olefin system.

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Chimie
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Dates et versions

hal-04490592 , version 1 (05-03-2024)

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Guillaume Ernouf, Egor Chirkin, Lydia Rhyman, Ponnadurai Ramasami, Jean‐christophe Cintrat. Photochemical Strain‐Release‐Driven Cyclobutylation of C(sp 3 )‐Centered Radicals. Angewandte Chemie International Edition, 2019, 59 (7), pp.2618-2622. ⟨10.1002/anie.201908951⟩. ⟨hal-04490592⟩
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