Copper-catalyzed coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation

被引：119

作者：

Niu, Mingyu ^{[1
]}

Yin, Zhengming ^{[2
]}

Fu, Hua ^{[1
]}

Jiang, Yuyang ^{[1
,3
]}

Zhao, Yufen ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Minist educ, Beijing 100084, Peoples R China

[2] Zhengzhou Univ, Dept Chem, Key Lab Chem Biol & Organ Chem, Zhengzhou 450052, Henan Province, Peoples R China

[3] Tsinghua Univ, Grad Sch Shenzhen, Key Lab Chem Biol, Shenzhen 518057, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 10期

关键词：

D O I：

10.1021/jo800279j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a convenient and efficient method for coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C-H activation. The protocol uses CuBr as the catalyst, NBS as the free radical initiator, CH3CN as the solvent, and the alkynylation was selectively performed on the methyl of tertiary aliphatic amines at 80 degrees C. This is an economical and practical method for the synthesis of propargylamines.

引用

页码：3961 / 3963

页数：3

共 89 条

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].

Ackermann, L ;

Althammer, A ;

Born, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622

[2] SELECTIVE INTERMOLECULAR CARBON-HYDROGEN BOND ACTIVATION BY SYNTHETIC METAL-COMPLEXES IN HOMOGENEOUS SOLUTION [J].

ARNDTSEN, BA ;

BERGMAN, RG ;

MOBLEY, TA ;

PETERSON, TH .

ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (03) :154-162

[3]

Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a

[4]

Boulton AA, 1997, DRUG DEVELOP RES, V42, P150, DOI 10.1002/(SICI)1098-2299(199711/12)42:3/4<150::AID-DDR6>3.0.CO

[5]

2-P

[6] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles [J].

Campos, Kevin R. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1069-1084

[7] Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].

Chatani, N ;

Asaumi, T ;

Yorimitsu, S ;

Ikeda, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941

[8] Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes [J].

Chatani, N ;

Asaumi, T ;

Ikeda, T ;

Yorimitsu, S ;

Ishii, Y ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12882-12883

[9] Thermal, catalytic, regiospecific functionalization of alkanes [J].

Chen, HY ;

Schlecht, S ;

Semple, TC ;

Hartwig, JF .

SCIENCE, 2000, 287 (5460) :1995-1997

[10] Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].

Chen, X ;

Li, JJ ;

Hao, XS ;

Goodhue, CE ;

Yu, JQ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79

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