Trichloroisocyanuric Acid (TCCA): A Suitable Reagent for the Synthesis of Selanyl-benzo[b]chalcogenophenes

被引：21
作者：
Blodorn, Gustavo B. [1 ]
Duarte, Luis Fernando B. [1 ]
Roehrs, Juliano A. [1 ,2 ]
Silva, Marcio S. [1 ]
Neto, Jose S. S. [3 ]
Alves, Diego [1 ]
机构：
[1] Univ Fed Pelotas UFPel, LASOL CCQFA, POB 354, BR-96010900 Pelotas, RS, Brazil
[2] Inst Fed Educ Ciencia & Tecnol Sul Rio Grandense, BR-96015360 Pelotas, RS, Brazil
[3] Univ Fed Santa Catarina, UFSC, Dept Quim, Florianopolis, SC, Brazil
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 40期
关键词：
Cyclization; Chalcogenophenes; Electrophilic addition; Selenium; Synthetic methods; ELECTROPHILIC CYCLIZATION; PROMOTED CYCLIZATION; ALKYNES; DERIVATIVES; ACCESS; DICHALCOGENIDES; ORGANOSELENIUM; HETEROCYCLES; BENZOFURAN; ANHYDRIDES;
D O I：
10.1002/ejoc.202200775
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new approach for the synthesis of 3-organoselanyl-benzo[b]chalcogenophenes promoted by trichloroisocyanuric acid is reported. The reaction was carried out with electrophilic selenium species which were generated in situ by the reaction between trichloroisocyanuric acid and diorganyl diselenides using ethanol as solvent. The developed method uses mild reaction conditions and was efficient for the synthesis of different 3-organoselanyl-benzo[b]chalcogenophenes in a good to excellent yields. Analysis of Se-77 NMR spectroscopy indicates that the electrophilic PhSeCl was formed in situ and a plausible reaction mechanism was proposed.
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页数：6
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