Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines

被引：389

作者：

Kwong, FY ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 06期

关键词：

D O I：

10.1021/ol0273396

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Graphics An efficient copper-catalyzed amination of aryl bromides with primary alkylamines was developed that uses commercially available diethylsalicylamide as the ligand. This amination reaction can be performed at 90 degreesC in good yield. A variety of functional groups are compatible with these reaction conditions. Preliminary results show that this reaction can be carried out under solvent-free conditions with comparable yields.

引用

收藏

页码：793 / 796

页数：4

相关论文

共 44 条

[1] Copper-catalyzed coupling of arylboronic acids and amines [J].

Antilla, JC ;

Buchwald, SL .

ORGANIC LETTERS, 2001, 3 (13) :2077-2079

[2] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[3] ULLMANN CONDENSATION REACTION OF HALOANTHRAQUINONE DERIVATIVES WITH AMINES IN APROTIC-SOLVENTS [J].

ARAI, S ;

YAMAGISHI, T ;

OTOTAKE, S ;

HIDA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (02) :547-548

[4] The chemistry of pentavalent organobismuth reagents .14. Recent advances in the copper-catalyzed phenylation of amines. [J].

Arnauld, T ;

Barton, DHR ;

Doris, E .

TETRAHEDRON, 1997, 53 (12) :4137-4144

[5] Catalytic amination of 5-iodouracil derivatives [J].

Arterburn, JB ;

Pannala, M ;

Gonzalez, AM .

TETRAHEDRON LETTERS, 2001, 42 (08) :1475-1477

[6] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[7]

Clement JB, 2001, SYNLETT, P1423

[8] The [Cu(OH)•TMEDA]2Cl2-catalyzed coupling of arylboronic acids with imidazoles in water [J].

Collman, JP ;

Zhong, M ;

Zeng, L ;

Costanzo, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1528-1531

[9] An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].

Collman, JP ;

Zhong, M .

ORGANIC LETTERS, 2000, 2 (09) :1233-1236

[10] N-arylation of primary and secondary aliphatic amines on solid supports [J].

Combs, AP ;

Tadesse, S ;

Rafalski, M ;

Haque, TS ;

Lam, PYS .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (02) :179-182

← 1 2 3 4 5 →