Visible Light Photocatalytic Reduction of O‐Thiocarbamates: Development of a Tin‐Free Barton–McCombie Deoxygenation Reaction. Issue 13 (11th September 2014)

• Record Type: Journal Article
• Authors: Chenneberg, Ludwig; Baralle, Alexandre; Daniel, Marion; Fensterbank, Louis; Goddard, Jean‐Philippe; Ollivier, Cyril
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 13(2014)
• Page Start: 2756
• Page End: 2762
• Publication Date: 2014-09-11
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400729
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The Barton–McCombie deoxygenation is one of the most important transformations in the toolbox of organic chemists which has been the subject of a number of methodological developments. In this study, we report a photocatalyzed redox deoxygenation of secondary and tertiary alcohols from thiocarbamate precursors under visible light activation. The iridium complex Ir(ppy)₃ proved to be the most efficient catalyst in the presence of Hünig's base as sacrifial electron donor. A mechanistic investigation is presented based on fluorescence quenching experiments and cyclic voltammetry.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh1c9js63k" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>