A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.
Thiiranes, the corresponding sulfur analogues of epoxides, are less studied and less encountered in literature. This might be due to the limited existing synthetic approaches for their synthesis. Herein, a mild, sustainable and efficient organocatalytic synthesis of thiiranes has been developed. Starting from olefins and utilizing the epoxidation protocol developed in the Kokotos’ group, which employs 2,2,2‐trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, followed by ring opening by thiourea, a variety of thiiranes were synthesized. Both aromatic and aliphatic moieties are well tolerated, leading to thiiranes in moderate to excellent yields.
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