An efficient electrochemical selenocyclization strategy for the synthesis of 3-selenylindoles from 2-ethynylanilines and diselenides has been developed in simple tube- or beaker-type undivided cells under ambient conditions. Notably, these sustainable transformations are completed within a short time with low equivalents of charges, diselenides and electrolytes, exhibiting a broad substrate scope with excellent functional group compatibility. Moreover, a gram-scale electrosynthesis and late-stage functionalization of complex molecules further demonstrate the practical synthetic potential of this facile electrochemical system.
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http://dx.doi.org/10.1039/d3ob01502e | DOI Listing |
Org Lett
January 2025
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal 741246, India.
An electrochemical strategy for the regioselective construction of seleno-benzothiophenes/furans is reported through electrochemical selenocyclization, followed by Wagner-Meerwein rearrangement. This electro-oxidative tandem process operates under metal-free and external chemical oxidant-free conditions. Advantageously, unprotected homopropargyl alcohols were found to be compatible under the reaction conditions, releasing water and dihydrogen as the biproduct.
View Article and Find Full Text PDFChemistry
June 2024
Yunnan Key Laboratory of Metal-Organic Molecular Materials and Device, School of Chemistry and Chemical Engineering, Kunming University, 2 Puxin Road, Kunming, 650214, China.
Three hybrid electrochemical protocols, which involve the energy transfer, direct photolysis and N-hydroxyphthalimide catalyst, respectively, are presented for the selenylation/cyclization of the fragile substrates of 3-aza-1,5-dienes with diorganyl diselenides to afford 3-selenomethyl-4-pyrrolin-2-ones. The two electrophotocatalytic reactions and the indirect electrolysis one are both regioselective and external-oxidant- and transition-metal-free, and are associated with a broad substrate scope and high Se-economy, and all three methods are amenable to gram-scale syntheses, late-stage functionalizations, sunlight-induced experiments and all-solar-driven syntheses.
View Article and Find Full Text PDFOrg Biomol Chem
November 2023
College of Education for the Future, Beijing Normal University, Zhuhai 519087, China.
An efficient electrochemical selenocyclization strategy for the synthesis of 3-selenylindoles from 2-ethynylanilines and diselenides has been developed in simple tube- or beaker-type undivided cells under ambient conditions. Notably, these sustainable transformations are completed within a short time with low equivalents of charges, diselenides and electrolytes, exhibiting a broad substrate scope with excellent functional group compatibility. Moreover, a gram-scale electrosynthesis and late-stage functionalization of complex molecules further demonstrate the practical synthetic potential of this facile electrochemical system.
View Article and Find Full Text PDFChem Asian J
December 2021
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246, West Bengal, India.
The current methodology reveals a green and proficient electro-oxidative tandem selenocyclization of thioallyl benzoimidazoles manufacturing selenylated dihydro-benzoimidazo-thiazine derivatives. Both C-Se and C-N bond formation were achieved via this mild protocol which exhibits good functional group tolerability affording an extensive range of substrate scope up to 96% isolated yields. Complete control over the regioselective formation of the six-membered heterocycle and stereoselective construction of the contiguous stereocenters was established.
View Article and Find Full Text PDFJ Org Chem
November 2021
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur 741246, West Bengal, India.
The current method represents an electrochemically driven synthetic route to access polysubstituted selenofuran derivatives through the diselenide-promoted cyclization of homopropargyl alcohols. The tandem electro-oxidative transformation operates at ambient temperature and in the absence of an external oxidant. This mild and efficient methodology exhibits good functional group compatibility, providing a broad range of substrate scopes up to 84% isolated yield.
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