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Intermolecular 1,2-difunctionalization of alkenes

Yuanrui Wang, Zhipeng Bao, Xu-Dong Mao, Ming Hou, Xiao‐Feng Wu

2025Chemical Society Reviews66 citationsDOIOpen Access PDF

Abstract

three different reaction modes. Firstly, metal species can add double bonds by employing transition metals; further coupling can then be followed to complete the difunctionalization. Another intriguing approach is that radicals add to the olefins and then are quenched in diverse ways. The ability to continuously introduce diverse functional groups is the most significant feature of this platform. The third mode is that the olefin is transformed into a cationic radical or anionic radical intermediate through single-electron transfer. This strategy is less developed and more novel, but has certain limitations. Driven by the innovation of synthetic chemistry strategies, the difunctionalization of olefins, which was previously difficult to achieve, has also been gradually achieved. This review updates the latest progress in the 1,2-difunctionalization of olefins in the past five years. We aim to classify reaction mechanisms and functional group types. It should be stated that reactions with olefin double bonds to form rings are not included here.

Topics & Concepts

Olefin fiberChemistryDouble bondCationic polymerizationRadicalIntermolecular forceFunctional groupMoleculeComputational chemistryCombinatorial chemistryGroup (periodic table)Coupling reactionReaction conditionsOrganic synthesisCoupling (piping)Reactive intermediatePhotochemistryOrganic chemistryOrganic moleculesCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisFluorine in Organic Chemistry