Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction

被引：12

作者：

Yamamoto, Yuki ^{[1
]}

Kawaguchi, Shin-ichi ^{[2
]}

Nishimura, Misaki ^{[1
]}

Sato, Yuki ^{[1
]}

Shimada, Yoshihisa ^{[1
]}

Tabuchi, Akihiro ^{[1
]}

Nomoto, Akihiro ^{[1
]}

Ogawa, Akiya ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Sakai, Osaka 5998531, Japan

[2] Saga Univ, Fac Agr, Ctr Educ & Res Agr Innovat, Saga 8470021, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 22期

基金：

日本学术振兴会;

关键词：

71;

D O I：

10.1021/acs.joc.0c01926

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：14684 / 14696

页数：13