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

preprint
submitted on 25.06.2019 and posted on 26.06.2019 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.

History

Email Address of Submitting Author

guillaume.ernouf@orange.fr

Institution

CEA, Université Paris-Saclay

Country

France

ORCID For Submitting Author

0000-0001-9279-6365

Declaration of Conflict of Interest

No conflict of interest

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in Angewandte Chemie International Edition

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