Solution phase combinatorial synthesis of biaryl libraries employing heterogeneous conditions for catalysis and isolation with size exclusion chromatography for purification

被引：46
作者：
Boger, DL
Goldberg, J
Andersson, CM
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[3] Lund Univ, S-22100 Lund, Sweden
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 07期
关键词：
D O I：
10.1021/jo982234v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and effective approach to the solution phase synthesis of biaryl libraries from iodoarenes is described enlisting 10% Pd-C as an inexpensive and readily available supported catalyst. Isolation and purification of small library mixtures, individual library members, and intermediates in the multistep sequence by a combination of liquid-liquid and liquid-solid extractions and size exclusion chromatography are detailed.
引用
收藏
页码：2422 / 2427
页数：6
相关论文
共 39 条
[1]   CARBON-CARBON BOND-FORMING METHODS ON SOLID SUPPORT - UTILIZATION OF KENNER SAFETY-CATCH LINKER [J].
BACKES, BJ ;
ELLMAN, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (24) :11171-11172
[2]  
Blettner CG, 1998, SYNLETT, P295
[3]   Higher order iminodiacetic acid libraries for probing protein-protein interactions [J].
Boger, DL ;
Goldberg, J ;
Jiang, WQ ;
Chai, WY ;
Ducray, P ;
Lee, JK ;
Ozer, RS ;
Andersson, CM .
BIOORGANIC & MEDICINAL CHEMISTRY, 1998, 6 (08) :1347-1378
[4]   Generation of targeted C-2-symmetrical compound libraries by solution-phase combinatorial chemistry [J].
Boger, DL ;
Ozer, RS ;
Andersson, CM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (14) :1903-1908
[5]   Higher order iminodiacetic acid libraries for probing protein-protein interactions [J].
Boger, DL ;
Ducray, P ;
Chai, WY ;
Jiang, WQ ;
Goldberg, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (17) :2339-2344
[6]   Solution-phase combinatorial synthesis via the olefin metathesis reaction [J].
Boger, DL ;
Chai, WY ;
Ozer, RS ;
Andersson, CM .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (04) :463-468
[7]   Synthesis of tetrasubstituted ethylenes on solid support via resin capture [J].
Brown, SD ;
Armstrong, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) :6331-6332
[8]   The Stille cross coupling reactions on solid support.: Link to solution phase directed ortho metalation.: An ester linker approach to styryl, biaryl and heterobiaryl carboxylic acids [J].
Chamoin, S ;
Houldsworth, S ;
Snieckus, V .
TETRAHEDRON LETTERS, 1998, 39 (24) :4175-4178
[9]   The Suzuki-Miyaura cross coupling reactions on solid support.: Link to solution phase directed ortho metalation.: The Leznoff acetal linker approach to biaryl and heterobiaryl aldehydes [J].
Chamoin, S ;
Houldsworth, S ;
Kruse, CG ;
Bakker, WI ;
Snieckus, V .
TETRAHEDRON LETTERS, 1998, 39 (24) :4179-4182
[10]  
CHENERA B, 1995, J AM CHEM SOC, V117, P11999
1234