Hydroiodination-Triggered Cascade Reaction with I2/PPh3/H2O: Metal-Free Access to 3-Substituted Phthalides from 2-Alkynylbenzoates

被引：8

作者：

Kawaguchi, Shin-ichi ^{[1
]}

Nakamura, Kentaro ^{[2
]}

Yamaguchi, Kotaro ^{[2
]}

Sato, Yuki ^{[2
]}

Gonda, Yuhei ^{[2
]}

Nishioka, Masaaki ^{[2
]}

Sonoda, Motohiro ^{[3
]}

Nomoto, Akihiro ^{[2
]}

Ogawa, Akiya ^{[2
]}

机构：

[1] Saga Univ, Fac Agr, Ctr Educ & Res Agr Innovat, 152-1 Shonan Cho, Karatsu, Saga 8470021, Japan

[2] Osaka Prefecture Univ, Grad Sch Engn, Dept Appl Chem, Naka Ku, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan

[3] Osaka Prefecture Univ, Grad Sch Life & Environm Sci, Dept Appl Biosci, Naka Ku, 1-1 Gakuen Cho, Sakai, Osaka 5998531, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 2017卷 / 36期

基金：

日本学术振兴会;

关键词：

Iodine-mediated reactions; Domino reactions; Cyclization; Reduction; Iodine; Phosphorus; ELECTROPHILIC CYCLIZATION; ALKYNES; IODINE; ISOBENZOFURAN-1(3H)-ONES; ISOBENZOFURANONES; LACTONIZATION; IODOALKENES; DERIVATIVES; CATALYST; ADDUCTS;

D O I：

10.1002/ejoc.201700839

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Phthalide is an important scaffold found in several biologically active compounds. Therefore, effective methods for the synthesis of phthalides are strongly desired. Herein, we describe the metal-free synthesis of 3-substituted phthalides by the reductive hydroiodination of 2-alkynylbenzoates through an I-2/PPh3/H2O-triggered cascade reaction. A variety of 3-substituted phthalides were synthesized in excellent yields by a onepot reaction involving four processes: desilylation, hydroiodination, cyclization, and reduction.

引用

页码：5343 / 5346

页数：4

共 41 条

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