Lithium bis-catechol borate as an effective reductive quencher in photoredox catalysis. Issue 26 (28th June 2018)

• Record Type: Journal Article
• Authors: Sevrin, Martin J.; Furst, Laura; Nguyen, John D.; Collins, James L.; Stephenson, Corey R.J.
• Is Part Of: Tetrahedron. Volume 74:Issue 26(2018)
• Page Start: 3246
• Page End: 3252
• Publication Date: 2018-06-28
• Subjects: Radical chemistry -- Photocatalysis -- Natural products; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.04.053
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The use of lithium bis-catechol borate (LiB(cat)2 ) as a reductive quencher for the photoredox mediated intermolecular C–H functionalization of various heteroaromatics with bromopyrroloindolines is described. LiB(cat)2 offers a financial benefit over state-of-the-art quenchers currently in use while eliminating the side reactions that typically plague these couplings. The advantage of this methodology is highlighted by the synthesis of C3–C2' (−) gliocladin C. Furthermore, additional examples of reactivity with various bromopyrroloindolines sets the stage for expedient routes towards other pharmaceutically active hexahydropyrroloindoline alkaloids and their analogues. Graphical abstract: Image 1