A Benzoyl Peroxide/Diphenyl Diselenide Binary System for Functionalization of Alkynes Leading to Alkenyl and Alkynyl Selenides
| Autor: | Tomokazu Saeki, Motohiro Sonoda, Akihiro Nomoto, Shintaro Kodama, Shinichi Kawaguchi, Akiya Ogawa, Kei Mihara, Shinya Higashimae |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
010405 organic chemistry
Chemistry Electrophilic addition Organic Chemistry Benzoyl peroxide 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Diselenide chemistry.chemical_compound Selenide medicine Organic chemistry Surface modification Organic synthesis Binary system Diphenyl diselenide medicine.drug |
| Zdroj: | The Journal of organic chemistry. 82(23) |
| ISSN: | 1520-6904 |
| Popis: | Binary systems consisting of benzoyl peroxide (BPO) and diorganyl diselenide are effective in the selective benzoyloxyselenation of internal alkynes to afford the corresponding β-(benzoyloxy)alkenyl selenides in good yields. In contrast to internal alkynes, terminal alkynes undergo a novel C(sp)–H substitution with the phenylseleno group of the BPO/(PhSe)2 system, providing alkynyl selenides in good yields. Both selenation reactions might proceed via benzoyloxy selenide (PhC(O)O–SeAr) as a key intermediate for electrophilic addition to alkynes. The products alkenyl and alkynyl selenides are expected to be useful synthetic intermediates in organic synthesis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|