Revisiting the Saito Photochemical Reduction and the Development of a One-Pot Deoxygenation of Alcohols

We have revisited the Saito photochemical reduction and established practical reaction conditions, under which the reduction of m‐(trifluoromethyl)benzoates, derived from secondary and tertiary alcohols, proceeds selectively at high concentration to afford the corresponding alkane products in good y...

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Veröffentlicht in:Asian journal of organic chemistry 2014-10, Vol.3 (10), p.1054-1057
Hauptverfasser: Matsubara, Ryosuke, Shin, Yong-Soon, Shimada, Toshiyuki, Hayashi, Masahiko
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Sprache:eng
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Zusammenfassung:We have revisited the Saito photochemical reduction and established practical reaction conditions, under which the reduction of m‐(trifluoromethyl)benzoates, derived from secondary and tertiary alcohols, proceeds selectively at high concentration to afford the corresponding alkane products in good yields without formation of alkenes. A one‐pot deoxygenation of alcohols to alkanes has also been developed. Concentrate on this one: The Saito photochemical reduction of m‐(trifluoromethyl)benzoates has been revisited. In contrast to the conventional conditions, the developed method eliminates the formation of alkene byproducts at high concentrations. Combining direct esterification and the Saito photochemical reduction, a one‐pot deoxygenation process of alcohols has also been developed. LED=light‐emitting diode; TsOH=4‐toluenesulfonic acid.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201402123