Electrochemical Annulation of ortho‐Alkynylbiphenyls to Fused Sulfenyl Phenanthrenes and Spiro Cyclohexenone Indenes
Anil Balajirao Dapkekar,
Jakkula Naveen,
Gedu Satyanarayana
Abstract:Here, we present an electrochemically induced synthesis of 9‐sulfenylarylphenanthrenes and 3’‐sulfenylarylspiro‐cyclohexa[4.5]trienones starting from o‐alkynylbiphenyls and diaryl disulfides. This method was accomplished through constant current electrolysis of 10 mA in an undivided cell setup by utilizing CH3CN as a solvent and LiClO4 as an electrolyte at room temperature. Notably, the present strategy enabled the formation of sulfenylphenanthrenes and sulfenyl spiro cyclohexa[4.5]trienones in 70%–95% yield. … Show more
“…32 Later, the research groups of Lie and Chen developed electrochemical techniques for oxyselenylation of styrenes by utilizing HFIP/CH 3 CN and CH 3 CN/H 2 O as solvent media for 4 h and 16 h, respectively (Scheme 1d). 33 Inspired by recent advances in the field of synthetic organic electrochemistry and issues associated with the prior conventional routes and our ongoing research interest in developing sustainable synthetic strategies, 34 here, we present a practical, affordable, and sustainable electrochemical approach to hydroxyselenylation of unactivated olefins using diaryl diselenides, in CH 3 CN solvent in an undivided cell (Scheme 1e). This method was amenable at ambient temperature without the requirement of an oxidant, a catalyst or an additive.…”
This work demonstrates the electrochemical construction of 2-methyl-1-aryloxy-3-(arylselanyl)propan-2-ol / 2-hydroxy-2-methyl-3-(arylselanyl)propyl 2-(2-hydroxy-2-methyl-3-(arylselanyl)propoxy)benzoate starting from aryl allyl ethers/allyl benzoates and diaryl diselenides under additive-free electrochemical conditions. This environmentally friendly method was achieved...
“…32 Later, the research groups of Lie and Chen developed electrochemical techniques for oxyselenylation of styrenes by utilizing HFIP/CH 3 CN and CH 3 CN/H 2 O as solvent media for 4 h and 16 h, respectively (Scheme 1d). 33 Inspired by recent advances in the field of synthetic organic electrochemistry and issues associated with the prior conventional routes and our ongoing research interest in developing sustainable synthetic strategies, 34 here, we present a practical, affordable, and sustainable electrochemical approach to hydroxyselenylation of unactivated olefins using diaryl diselenides, in CH 3 CN solvent in an undivided cell (Scheme 1e). This method was amenable at ambient temperature without the requirement of an oxidant, a catalyst or an additive.…”
This work demonstrates the electrochemical construction of 2-methyl-1-aryloxy-3-(arylselanyl)propan-2-ol / 2-hydroxy-2-methyl-3-(arylselanyl)propyl 2-(2-hydroxy-2-methyl-3-(arylselanyl)propoxy)benzoate starting from aryl allyl ethers/allyl benzoates and diaryl diselenides under additive-free electrochemical conditions. This environmentally friendly method was achieved...
Alkynes are important in organic synthesis. This review mainly focus on recent advances (2013-2023) of alkynes with C-S bond formation, based on more than 30 kinds of sulfur reagents. Diverse...
Herein, we have developed an electrochemical technique that enables the regioselective construction of 4-sulfenyl-1H-isochromen-1-ones in an undivided cell under external acid, catalyst, oxidant, or metal-free conditions.
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