Bronsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature

被引：56

作者：

Hyodo, Kengo ^{[1
]}

Togashi, Kosuke ^{[1
]}

Oishi, Naoki ^{[1
]}

Hasegawa, Genna ^{[1
]}

Uchida, Kingo ^{[1
]}

机构：

[1] Ryukoku Univ, Fac Sci & Technol, Dept Mat Chem, Otsu, Shiga 5202194, Japan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 11期

关键词：

SELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; MILD CONDITIONS; METHYL ARENES; DEHYDRATION; ALDOXIMES; ALCOHOLS; CONVERSION; TRANSFORMATION; CONVENIENT;

D O I：

10.1021/acs.orglett.7b01263

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Bronsted acid-catalyzed synthesis of nitriles is described via transoximation under mild conditions using an O-protected oxime as a more stable equivalent of explosive O-protected hydroxylamines. The nitrile was generated via an O-protected aldoxime produced from the aldehyde and an O-protected oxime through transoximation. The reaction could be performed on a 1 g scale.

引用

页码：3005 / 3008

页数：4

共 43 条

[41] A General and Convenient Catalytic Synthesis of Nitriles from Amides and Silanes
Zhou, Shaolin
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[J]. ORGANIC LETTERS, 2009, 11 (11) : 2461 - 2464
[42] Direct Transformation of Methyl Arenes to Aryl Nitriles at Room Temperature
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[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) : 7094 - 7097
[43] Tin or gallium-catalyzed cyanide-transition metal-free synthesis of nitriles from aldehydes or oximes
Zhuang, Yan-Jun
Liu, Jie
Kang, Yan-Biao
[J]. TETRAHEDRON LETTERS, 2016, 57 (50) : 5700 - 5702

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