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A Benzoyl Peroxide/Diphenyl Diselenide Binary System for Functionalization of Alkynes Leading to Alkenyl and Alkynyl Selenides

Author:
Kodama, Shintaro, Saeki, Tomokazu, Mihara, Kei, Higashimae, Shinya, Kawaguchi, Shin-ichi, Sonoda, Motohiro, Nomoto, Akihiro, Ogawa, Akiya
Source:
Journal of organic chemistry 2017 v.82 no.23 pp. 12477-12484
ISSN:
1520-6904
Subject:
Lewis acids, alkynes, chemical reactions, chemical structure, organic chemistry
Abstract:
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.
Agid:
5864564