Palladium-catalyzed couplings of heteroaryl amines with aryl halides using sodium phenolate as the stoichiometric base

被引:30
作者
Schulte, James P., II [1 ]
Tweedie, Scott R. [1 ]
机构
[1] Albany Mol Res Inc, Albany, NY 12203 USA
关键词
palladium-catalyzed; sodium phenolate; C-N bondforming; biaryl arnine; heteroaryl amine;
D O I
10.1055/s-2007-985597
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heteroaryl amines are efficiently coupled (in two hours) to aryl halides with catalytic Pd(2()dba)(3) and Xantphos to provide the corresponding biaryl amines under microwave and standard thermal conditions. The use of organic-soluble sodium phenolate (NaOPh) as the stoichiometric base promotes facile coupling of a variety of substrates in excellent yields.
引用
收藏
页码:2331 / 2336
页数:6
相关论文
共 24 条
[1]   Mechanism of aryl chloride amination: Base-induced oxidative addition [J].
Alcazar-Roman, LM ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12905-12906
[2]   An improved method for the palladium-catalyzed amination of aryl iodides [J].
Ali, MH ;
Buchwald, SL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2560-2565
[3]   Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].
Anderson, Kevin W. ;
Tundel, Rachel E. ;
Ikawa, Takashi ;
Altman, Ryan A. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527
[4]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[5]   Imidazo[1,2-α]pyridines.: Part 2:: SAR and optimisation of a potent and selective class of cyclin-dependent kinase inhibitors [J].
Byth, KF ;
Culshaw, JD ;
Green, S ;
Oakes, SE ;
Thomas, AP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (09) :2245-2248
[6]   Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].
Hartwig, JF ;
Kawatsura, M ;
Hauck, SI ;
Shaughnessy, KH ;
Alcazar-Roman, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580
[7]   Rapid and efficient microwave-assisted synthesis of aryl aminobenzophenones using Pd-catalyzed Amination [J].
Jensen, TA ;
Liang, XF ;
Tanner, D ;
Skjaerbaek, N .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4936-4947
[8]   Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings [J].
Kataoka, N ;
Shelby, Q ;
Stambuli, JP ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5553-5566
[9]  
Kim K.S., 2001, [No title captured], Patent No. [US 6 262 096B1, 6262096]
[10]  
KOMATSU A, 1975, Patent No. 3859374