Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines

被引:42
作者
Quan, Zheng-Jun [1 ]
Jing, Fu-Qiang [1 ]
Zhang, Zhang [1 ]
Da, Yu-Xia [1 ]
Wang, Xi-Cun [1 ]
机构
[1] Northwest Normal Univ, Lab Ecoenvironm Related Polymer Mat, Coll Chem & Chem Engn, Minist Educ,Gansu Key Lab Polymer Mat, Lanzhou 730070, Gansu, Peoples R China
关键词
Synthetic methods; C-C coupling; Cross-coupling; Nitrogen heterocycles; Palladium; Alkynes; CALCIUM-CHANNEL BLOCKERS; SUZUKI-MIYAURA; ARYLBORONIC ACIDS; CARBON-CARBON; BIGINELLI 3,4-DIHYDROPYRIMIDIN-2(1H)-ONE; ARYL IMIDAZOLYLSULFONATES; SONOGASHIRA REACTIONS; PHASE SYNTHESIS; BORONIC ACIDS; SOLID-PHASE;
D O I
10.1002/ejoc.201300592
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)(2)-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized.
引用
收藏
页码:7175 / 7183
页数:9
相关论文
共 92 条
[1]   Palladium-Catalyzed Direct C-H Bond Alkynylations of Heteroarenes Using gem-Dichloroalkenes [J].
Ackermann, Lutz ;
Kornhaass, Christoph ;
Zhu, Yingjun .
ORGANIC LETTERS, 2012, 14 (07) :1824-1826
[2]   Palladium- and Nickel-Catalyzed Aminations of Aryl Imidazolylsulfonates and Sulfamates [J].
Ackermann, Lutz ;
Sandmann, Rene ;
Song, Weifeng .
ORGANIC LETTERS, 2011, 13 (07) :1784-1786
[3]   Palladium-catalyzed sequential alkylation-alkenylation reactions: application towards the synthesis of polyfunctionalized fused aromatic rings [J].
Alberico, D ;
Paquin, JF ;
Lautens, M .
TETRAHEDRON, 2005, 61 (26) :6283-6297
[4]   One-Pot Double Suzuki Couplings of Dichloropyrimidines [J].
Anderson, Samantha C. ;
Handy, Scott T. .
SYNTHESIS-STUTTGART, 2010, (16) :2721-2724
[5]  
[Anonymous], 2007, ANGEW CHEM
[6]  
[Anonymous], 2004, METAL CATALYZED CROS
[7]  
[Anonymous], 2004, METAL CATALYZED CROS
[8]   DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].
ATWAL, KS ;
SWANSON, BN ;
UNGER, SE ;
FLOYD, DM ;
MORELAND, S ;
HEDBERG, A ;
OREILLY, BC .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811
[9]   Rapid Nickel-Catalyzed Suzuki-Miyaura Cross-Couplings of Aryl Carbamates and Sulfamates Utilizing Microwave Heating [J].
Baghbanzadeh, Mostafa ;
Pilger, Christian ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05) :1507-1510
[10]   Sequential Palladium-Catalysed Direct Arylation Followed by Suzuki Coupling of Bromo-2-chloropyridines: Simple Access to a Variety of 2-Arylpyridines [J].
Baloch, Marya ;
Roy, David ;
Bensaid, Souhila ;
Guerchais, Veronique ;
Doucet, Henri .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (28) :4454-4462