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Dealkenylative Functionalizations: Conversion of Alkene C(sp3)–C(sp2) Bonds into C(sp3)–X Bonds via Redox-Based Radical Processes

Ohyun Kwon, Brady W. Dehnert, Jeremy H Dworkin

2023Synthesis17 citationsDOIOpen Access PDF

Abstract

Abstract This review highlights the history and recent advances in dealkenylative functionalization. Through this deconstructive strategy, radical functionalizations occur under mild, robust conditions. The reactions described proceed with high efficiency, good stereoselectivity, tolerate many functional groups, and are completed within a matter of minutes. By cleaving the C(sp3)–C(sp2) bond of terpenes and terpenoid-derived precursors, rapid diversification of natural products is possible. 1 Introduction 2 Mechanism 3 History 4 Motivation to Pursue Dealkenylation 5 Dealkenylation in the Present 6 Conclusion

Topics & Concepts

ChemistryAlkeneSurface modificationRedoxStereoselectivityTerpeneOrganic chemistryMedicinal chemistryCombinatorial chemistryStereochemistryCatalysisPhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
Dealkenylative Functionalizations: Conversion of Alkene C(sp3)–C(sp2) Bonds into C(sp3)–X Bonds via Redox-Based Radical Processes | Litcius