Copper-catalyzed coupling of arylboronic acids and amines

被引:244
作者
Antilla, JC [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ol0160396
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A general catalytic coupling of arylboronic acids and amines is reported. This room-temperature coupling was realized through the use of catalytic copper(II) acetate, 2,6-lutidine as base, and myristic acid as an additive. Functionalized aniline substrates provided the diarylamine coupling products in good yield (58-91%), A variety of alkylamines were also successfully coupled to give N-alkyl anilines in moderate yield (50-64%).
引用
收藏
页码:2077 / 2079
页数:3
相关论文
共 26 条
[1]  
[Anonymous], 1993, Agrochemicals desk reference
[2]   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
[3]   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
[4]   An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].
Collman, JP ;
Zhong, M .
ORGANIC LETTERS, 2000, 2 (09) :1233-1236
[5]   First combined selective N- and C-arylations with boronic acids: application to the synthesis of 1,3-diarylindazoles [J].
Collot, V ;
Bovy, PR ;
Rault, S .
TETRAHEDRON LETTERS, 2000, 41 (47) :9053-9057
[6]   Solid supported aryl/heteroaryl C-N cross-coupling reactions. [J].
Combs, AP ;
Saubern, S ;
Rafalski, M ;
Lam, PYS .
TETRAHEDRON LETTERS, 1999, 40 (09) :1623-1626
[7]   Cupric acetate mediated N-arylation by arylboronic acids: A preliminary investigation into the scope of application [J].
Cundy, DJ ;
Forsyth, SA .
TETRAHEDRON LETTERS, 1998, 39 (43) :7979-7982
[8]   SYNTHESIS AND CHARACTERIZATION OF POLYANILINE DERIVATIVES - POLY(2-ALKOXYANILINES) AND POLY(2,5-DIALKOXYANILINES) [J].
DAPRANO, G ;
LECLERC, M ;
ZOTTI, G ;
SCHIAVON, G .
CHEMISTRY OF MATERIALS, 1995, 7 (01) :33-42
[9]   Complete N-1 regiocontrol in the formation of N-arylimidazoles.: Synthesis of the active site His-Tyr side chain coupled dipeptide of cytochrome c oxidase [J].
Elliott, GI ;
Konopelski, JP .
ORGANIC LETTERS, 2000, 2 (20) :3055-3057
[10]   Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].
Evans, DA ;
Katz, JL ;
West, TR .
TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940