Organocopper(ii) complexes: new catalysts for carbon–carbon bond formation via electrochemical atom transfer radical addition (eATRA). Issue 35 (26th August 2022)

• Record Type: Journal Article
• Authors: Gonzálvez, Miguel A.; Su, Chuyi; Williams, Craig M.; Bernhardt, Paul V.
• Is Part Of: Chemical science. Volume 13:Issue 35(2022)
• Page Start: 10506
• Page End: 10511
• Publication Date: 2022-08-26
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc03418b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Electrochemical generation of a novel organocopper(ii ) complex offers a new way to carry out atom transfer radical addition to alkenes under mild conditions with high yields and low catalyst loadings. Abstract : Organocopper(ii ) complexes are a rarity while organocopper(i ) complexes are commonplace in chemical synthesis. In the course of building a strategy to generate organocopper(ii ) species utilizing electrochemistry, a method to form compounds with Cu II –C bonds was discovered, that demonstrated remarkably potent reactivity towards different functionalized alkenes under catalytic control. The role of the organocopper(ii ) complex is to act as a source of masked radicals (in this case ˙CH2 CN) that react with an alkene to generate the corresponding γ-halonitrile in good yields through atom transfer radical addition (ATRA) to various alkenes. The organocopper(ii ) complexes can be continuously regenerated electrochemically for ATRA ( e ATRA), which proceeds at room temperature, under low Cu loadings (1–10 mol%) and with the possibility of Cu-catalyst recovery.