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Photochemical Strain-Release Driven Cyclobutylation of C(sp3)-centered radicals - Preprint.pdf (696.99 kB)

Photochemical Strain-Release Driven Cyclobutylation of C(sp3)-Centered Radicals

submitted on 25.06.2019, 21:43 and posted on 26.06.2019, 13:46 by Guillaume Ernouf, Egor Chirkin, Lydia Rhyman, Ponnadurai Ramasami, Jean-Christophe Cintrat
Our manuscript describes a photoredox-catalyzed decarboxylative radical addition approach to functionalized cyclobutanes. The reaction involves an unprecedented formal Giese-type addition of C(sp3)-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 access 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.


Email Address of Submitting Author


CEA, Université Paris-Saclay



ORCID For Submitting Author


Declaration of Conflict of Interest

No conflict of interest


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in Angewandte Chemie International Edition

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