Abstract
Oxidative potential of trans‐3,5‐dihydroperoxy‐3,5‐dimethyl‐1,2‐dioxolane (DHPODMDO) has been explored in the facile thiocyanation of anilines and indoles through the efficient and in situ generation of SCN+ ion from sodium thiocyanate. The reactions proceed with regioselectivity under mild conditions at room temperature to afford the respective thiocyanate derivatives in excellent yields and low reaction times.
Highlights
Organic thiocyanates are well-documented and important industrial compounds [1]
Following our ongoing research on the synthesis of gem-dihydroperoxides [31,32,33,34], and their applications in a variety of organic conversions including oxidation of alcohols to ketones [35], selective sulfoxidation of sufides [36], selective halogenation of aromatic compounds [37], epoxidation of α,β-unsaturated ketones [38], oxidative conversion of aldehydes, amines, alcohols and halides to nitriles [39], ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives [40], and synthesis of benzimidazoles and benzothiazoles [41], we were encouraged to study the oxidative potential of trans‐3,5‐dihydroperoxy‐3,5‐dimethyl‐1,2‐dioxolane (DHPDMDO) for thiocyanation of anilines and their related heterocyclic compounds such as indoles
NaSCN has been used as the source of HOSCN which is produced upon the initial degradation of trans‐3,5‐dihydroperoxy‐3,5‐dimethyl‐1,2‐dioxolane with NaSCN
Summary
Organic thiocyanates are well-documented and important industrial compounds [1]. These compounds have played important roles in the synthesis of organic compounds and various pharmaceutically important products [2]. Several methods have been reviewed in the literature for thiocyanation of aromatic and heteroaromatic systems including cross-coupling reaction of arylboronic acids with different reagents such as KSCN [7], sodium perborate [8], diethyl azodicarboxylate [9], Imidazolium-based phosphinite ionic liquid (IL-OPPh2) [10], I2O5 [11], 2-iodobenzoic acid [12], Br2/KSCN (only for indoles) [13], ceric ammonium nitrate (CAN) [14], trichloroisocyanuric acid/ammonium thiocyanate/wet SiO2 [15], and silica boron sulfonic acid Following our ongoing research on the synthesis of gem-dihydroperoxides [31,32,33,34], and their applications in a variety of organic conversions including oxidation of alcohols to ketones [35], selective sulfoxidation of sufides [36], selective halogenation of aromatic compounds [37], epoxidation of α,β-unsaturated ketones [38], oxidative conversion of aldehydes, amines, alcohols and halides to nitriles [39], ultrasound-accelerated selective oxidation of primary aromatic amines to azoxy derivatives [40], and synthesis of benzimidazoles and benzothiazoles [41], we were encouraged to study the oxidative potential of trans‐3,5‐dihydroperoxy‐3,5‐dimethyl‐1,2‐dioxolane (DHPDMDO) for thiocyanation of anilines and their related heterocyclic compounds such as indoles
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