C(sp3)–C(sp3) coupling of non-activated alkyl-iodides with electron-deficient alkenes via visible-light/silane-mediated alkyl-radical formation. Issue 44 (4th November 2022)

• Record Type: Journal Article
• Authors: Mistry, Sanesh; Kumar, Roopender; Lister, Andrew; Gaunt, Matthew J.
• Is Part Of: Chemical science. Volume 13:Issue 44(2022)
• Page Start: 13241
• Page End: 13247
• Publication Date: 2022-11-04
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc03516b
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Here, we present a remarkably mild and general initiation protocol for alkyl-radical generation from non-activated alkyl-iodides. Abstract : Here, we present a remarkably mild and general initiation protocol for alkyl-radical generation from non-activated alkyl-iodides. An interaction between a silane and an alkyl iodide is excited by irradiation with visible light to trigger carbon–iodide bond homolysis and form the alkyl radical. We show how this method can be developed into an operationally simple and general Giese addition reaction that can tolerate a range of sensitive functionalities not normally explored in established approaches to this strategically important transformation. The new method requires no photocatalyst or other additives and uses only commerical tris(trimethylsilyl)silane and visible light to effectively combine a broad range of alkyl halides with activated alkenes to form C(sp 3 )–C(sp 3 ) bonds embedded within complex frameworks.