Copper(II)-catalyzed dehydration of primary amides to nitriles with the aid of trichloroacetonitrile

被引：0

作者：

Ma, Xiaoyun ^{[1
]}

Wan, Xiaoyan ^{[1
]}

Zhao, Jun ^{[1
]}

机构：

[1] Guizhou Educ Univ, Sch Chem & Mat Sci, Guiyang, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2024年 / 54卷 / 22期

关键词：

Nitrile; amide; trichloroacetonitrile; cupric acetate; trichloroacetamide; MILD; ALDOXIMES;

D O I：

10.1080/00397911.2024.2415442

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the preparation of nitriles from primary amides using trichloroacetonitrile and a catalytic amount of cupric acetate is described. Using this method, amides including aromatic amides, aromatic heterocyclic amides and aliphatic amides were converted into the corresponding nitriles in moderate to good yields. Trichloroacetonitrile reacted with amide in the presence of cupric acetate to form trichloroacetamide, which has been isolated and confirmed.

引用

页码：1950 / 1958

页数：9

共 29 条

[1] Metal-Catalyzed Dehydration of Primary Amides to Nitriles [J].

Al-Huniti, Mohammed H. ;

Croatt, Mitchell P. .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (10) :1791-1799

[2] Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides To Form Nitriles [J].

Al-Huniti, Mohammed H. ;

Rivera-Chavez, Jose ;

Colon, Katsuya L. ;

Stanley, Jarrod L. ;

Burdette, Joanna E. ;

Pearce, Cedric J. ;

Oberlies, Nicholas H. ;

Croatt, Mitchell P. .

ORGANIC LETTERS, 2018, 20 (19) :6046-6050

[3]

ATTANASI O, 1983, SYNTHESIS-STUTTGART, P741

[4] AlCl3•6H2O/KI/H2O/CH3CN:: A new alternate system for dehydration of oximes and amides in hydrated media [J].

Boruah, M ;

Konwar, D .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7138-7139

[5]

Bose DS, 1999, SYNTHESIS-STUTTGART, P64

[6]

CAMPAGNA F, 1977, TETRAHEDRON LETT, P1813

[7] Primary amides to amines or nitriles: a dual role by a single catalyst [J].

Das, Hari S. ;

Das, Shyamal ;

Dey, Kartick ;

Singh, Bhagat ;

Haridasan, Rahul K. ;

Das, Arpan ;

Ahmed, Jasimuddin ;

Mandal, Swadhin K. .

CHEMICAL COMMUNICATIONS, 2019, 55 (79) :11868-11871

[8] NITRILE SYNTHESIS - DEHYDRATION OF AMIDES BY SILAZANES, CHLOROSILANES, ALKOXYSILANES, AND AMINOSILANES [J].

DENNIS, WE .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3253-&

[9] Synthesis of Nitriles from Primary Amides or Aldoximes under Conditions of a Catalytic Swern Oxidation [J].

Ding, Rui ;

Liu, Yongguo ;

Han, Mengru ;

Jiao, Wenyi ;

Li, Jiaqi ;

Tian, Hongyu ;

Sun, Baoguo .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20) :12939-12944

[10] DEHYDRATION OF PRIMARY AMIDES WITH SODIUM BOROHYDRIDE [J].

ELLZEY, SE ;

MACK, CH ;

CONNICK, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (03) :846-&

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