Palladium-Catalyzed Cyanothiolation of Internal Alkynes Using Organic Disulfides and tert-Butyl Isocyanide

被引：24

作者：

Higashimae, Shinya ^{[1
]}

Kurata, Daichi ^{[1
]}

Kawaguchi, Shin-ichi ^{[2
]}

Kodama, Shintaro ^{[1
]}

Sonoda, Motohiro ^{[3
]}

Nomoto, Akihiro ^{[1
]}

Ogawa, Akiya ^{[1
]}

机构：

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

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

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 09期

关键词：

HIGHLY REGIOSELECTIVE CYANOTHIOLATION; CARBON TRIPLE BONDS; C-H CYANATION; TRIMETHYLSILYL CYANIDE; CYANOGEN IODIDE; INTRAMOLECULAR AMINOCYANATION; STEREOSELECTIVE-SYNTHESIS; TERMINAL ACETYLENES; ADDITION-REACTIONS; NITRILES;

D O I：

10.1021/acs.joc.8b00052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Despite the availability of selective synthetic approaches to multifunctionalized substituted olefins, the cyanothiolation of internal alkynes has been much less explored. Herein, we show that nonactivated internal alkynes can be successfully cyanothiolated with diaryl disulfides and tert-butyl isocyanide in the presence of a Pd catalyst (e.g., Pd(PPh3)(4)) with the release of isobutene and arenethiol to afford beta-thiolated alkenyl cyanides in yields of 34-89%.

引用

页码：5267 / 5273

页数：7

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