Heteroaryl Ethers by Oxidative Palladium Catalysis of Pyridotriazol-1-yloxy Pyrimidines with Arylboronic Acids

被引:13
作者
Bardhan, Sujata [1 ]
Wacharasindhu, Sumrit [1 ]
Wan, Zhao-Kui [1 ]
Mansour, Tarek S. [1 ]
机构
[1] Wyeth Res, Chem Sci, Pearl River, NY 10965 USA
关键词
ARYL BORONIC ACIDS; C-O BOND; BASE-FREE; COUPLING REAGENTS; SNAR REACTIONS; AMINO-ACIDS; EFFICIENT; DERIVATIVES; HETEROCYCLES; ACTIVATION;
D O I
10.1021/ol900592b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The oxidative palladium-catalyzed cross-coupling of pyrimidines containing pyridotriazol-1-yloxy (OPt) as either a urea or an amide functional group with arylboronic acids in the presence of CS2CO3 in DME containing 0.6-1.0% H2O is described for the preparation of heteroaryl ethers. The bromo substitution in the case of 3-(5-bromo-pyrimidin-2-yloxy)-3H-[1,2,3]triazolo[4,5-b]pyridine 1 could serve as a handle for further elaborations such as Suzuki coupling for attaching varied aryl groups.
引用
收藏
页码:2511 / 2514
页数:4
相关论文
共 42 条
[1]   Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex [J].
Adamo, Carlo ;
Amatore, Christian ;
Ciofini, Ilaria ;
Jutand, Anny ;
Lakmini, Hakim .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6829-6836
[2]  
ALSINA J, 1996, TETRAHEDRON LETT, V37, P4174
[3]   Cu-catalyzed N- and O-arylation of 2-, 3-, and 4-hydroxypyridines and hydroxyquinolines [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (04) :643-646
[4]   Electrospray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids [J].
Aramendía, MA ;
Lafont, F ;
Moreno-Mañas, M ;
Pleixats, R ;
Roglans, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3592-3594
[5]   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
[6]   Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst [J].
Berthiol, F ;
Feuerstein, M ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2002, 43 (32) :5625-5628
[7]   Oxidation of complexes by (O2CPh)2 and (ER)2 (E = S, Se), including structures of Pd(CH2CH2CH2CH2)(SePh)2(bpy) (bpy = 2,2′-bipyridine) and MMe2(SePh)2(L2) (M = Pd, Pt; L2 = bpy, 1,10-phenanthroline) and C•••O and C•••E bond formation at palladium(IV) [J].
Canty, AJ ;
Jin, H ;
Skelton, BW ;
White, AH .
INORGANIC CHEMISTRY, 1998, 37 (16) :3975-3981
[8]   Synthesis of densely functionalised arenes using [2+2+2] cycloaddition reactions [J].
Clayden, Jonathan ;
Moran, Wesley J. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (07) :1028-1030
[9]   OXYBENZOTRIAZOLE FREE PEPTIDE COUPLING REAGENTS FOR N-METHYLATED AMINO-ACIDS [J].
COSTE, J ;
FREROT, E ;
JOUIN, P ;
CASTRO, B .
TETRAHEDRON LETTERS, 1991, 32 (17) :1967-1970
[10]   Insertion of O2 into a Pd(I)-Pd(I) dimer and subsequent C-O bond formation by activation of a C-H bond [J].
Durà-Vilà, V ;
Mingos, DMP ;
Vilar, R ;
White, AJP ;
Williams, DJ .
CHEMICAL COMMUNICATIONS, 2000, (16) :1525-1526