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Formal Cycloadditions Driven by the Homolytic Opening of Strained, Saturated Ring Systems
dc.contributor.authorHarmata, Alexander S.
dc.contributor.authorRoldan, B. J.
dc.contributor.authorStephenson, Corey R. J.
dc.date.accessioned2023-02-01T18:58:13Z
dc.date.available2024-02-01 13:58:09en
dc.date.available2023-02-01T18:58:13Z
dc.date.issued2023-01-23
dc.identifier.citationHarmata, Alexander S.; Roldan, B. J.; Stephenson, Corey R. J. (2023). "Formal Cycloadditions Driven by the Homolytic Opening of Strained, Saturated Ring Systems." Angewandte Chemie International Edition 62(4): n/a-n/a.
dc.identifier.issn1433-7851
dc.identifier.issn1521-3773
dc.identifier.urihttps://hdl.handle.net/2027.42/175764
dc.description.abstractThe field of strain-driven, radical formal cycloadditions is experiencing a surge in activity motivated by a renaissance in free radical chemistry and growing demand for sp3-rich ring systems. The former has been driven in large part by the rise of photoredox catalysis, and the latter by adoption of the “Escape from Flatland” concept in medicinal chemistry. In the years since these broader trends emerged, dozens of formal cycloadditions, including catalytic, asymmetric variants, have been developed that operate via radical mechanisms. While cyclopropanes have been studied most extensively, a variety of strained ring systems are amenable to the design of analogous reactions. Many of these processes generate lucrative, functionally decorated sp3-rich ring systems that are difficult to access by other means. Herein, we summarize recent efforts in this area and analyze the state of the field.Ring strain provides a driving force for the formation of reactive intermediates. Bonds of strained rings may undergo homolysis upon thermolysis, photolysis, radical addition, or following single electron transfer events. Regardless of homolytic method, intermediates competent in formal cycloaddition can be formed. Herein, we describe formal cycloadditions of strained systems operating via radical pathways.
dc.publisherWiley Periodicals, Inc.
dc.subject.otherStrained Rings
dc.subject.otherStrain-Driven
dc.subject.otherRadicals
dc.subject.otherCycloaddition
dc.titleFormal Cycloadditions Driven by the Homolytic Opening of Strained, Saturated Ring Systems
dc.typeArticle
dc.rights.robotsIndexNoFollow
dc.subject.hlbsecondlevelChemistry
dc.subject.hlbtoplevelScience
dc.description.peerreviewedPeer Reviewed
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/175764/1/anie202213003.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/175764/2/anie202213003_am.pdf
dc.identifier.doi10.1002/anie.202213003
dc.identifier.sourceAngewandte Chemie International Edition
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