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Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

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JournalACS Catalysis
DateAccepted/In press - 17 Apr 2020
DateE-pub ahead of print - 17 Apr 2020
DatePublished (current) - 15 May 2020
Issue number10
Volume10
Number of pages7
Pages (from-to)5814-5820
Early online date17/04/20
Original languageEnglish

Abstract

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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