Journal
ACS CATALYSIS
Volume 10, Issue 10, Pages 5814-5820Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c00690
Keywords
sulfoxide; deoxygenation; reduction; radical; visible light; photoredox catalysis; sulfide radical cation
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Funding
- EPSRC [EP/R013748/1]
- University of York
- Leverhulme Trust [ECF-2015-013]
- Department of Chemistry, University of York
- EPSRC [EP/R013748/1] Funding Source: UKRI
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The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)(2)(dtbbpy)]PF6 or fac-Ir(ppy)(3) is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/ polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.
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