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

発表形態:
原著論文
主要業績:
主要業績
単著・共著:
共著
発表年月:
2017年12月
DOI:
10.1021/acs.joc.7b02276
会議属性:
指定なし
査読:
有り
リンク情報:

日本語フィールド

著者:
Kodama, Shintaro; Saeki, Tomokazu; Mihara, Kei; Higashimae, Shinya; Kawaguchi, Shin Ichi; Sonoda, Motohiro; Nomoto, Akihiro; Ogawa, Akiya
題名:
A Benzoyl Peroxide/Diphenyl Diselenide Binary System for Functionalization of Alkynes Leading to Alkenyl and Alkynyl Selenides
発表情報:
Journal of Organic Chemistry 巻: 82 号: 23 ページ: 1247712484
キーワード:
概要:
© 2017 American Chemical Society. 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.
抄録:

英語フィールド

Author:
Kodama, Shintaro; Saeki, Tomokazu; Mihara, Kei; Higashimae, Shinya; Kawaguchi, Shin Ichi; Sonoda, Motohiro; Nomoto, Akihiro; Ogawa, Akiya
Title:
A Benzoyl Peroxide/Diphenyl Diselenide Binary System for Functionalization of Alkynes Leading to Alkenyl and Alkynyl Selenides
Announcement information:
Journal of Organic Chemistry Vol: 82 Issue: 23 Page: 1247712484
An abstract:
© 2017 American Chemical Society. 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.


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