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Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction

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:
2020年11月
DOI:
10.1021/acs.joc.0c01926
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:
Yamamoto, Yuki; Kawaguchi, Shin Ichi; Nishimura, Misaki; Sato, Yuki; Shimada, Yoshihisa; Tabuchi, Akihiro; Nomoto, Akihiro; Ogawa, Akiya
題名:
Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
発表情報:
Journal of Organic Chemistry 巻: 85 号: 22 ページ: 14684 - 14696
キーワード:
概要:
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.
抄録:

英語フィールド

Author:
Yamamoto, Yuki; Kawaguchi, Shin Ichi; Nishimura, Misaki; Sato, Yuki; Shimada, Yoshihisa; Tabuchi, Akihiro; Nomoto, Akihiro; Ogawa, Akiya
Title:
Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
Announcement information:
Journal of Organic Chemistry Vol: 85 Issue: 22 Page: 14684 - 14696
An abstract:
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.


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