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

26 June 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


photoredox reaction


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