Palladium(0)-catalyzed arylation of resin-bound imidazol-2-ylzinc chlorides

被引：0

作者：

Havez, S

Begtrup, M

Vedso, P

Andersen, K

Ruhland, T

机构：

[1] Royal Danish Sch Pharm, Dept Med Chem, DK-2100 Copenhagen, Denmark

[2] H Lundbeck AS, Med Chem Res, DK-2500 Valby, Denmark

来源：

SYNTHESIS-STUTTGART | 2001年 / 06期

关键词：

solid-phase synthesis; cross-coupling; palladium; zinc compounds; 1-hydroxyimidazole;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Hydroxyimidazole loaded on Wang resin under Mitsunobu conditions was selectively deprotonated at C-2 by BuLi. The anion formed was then reacted with electrophiles or transmetallated with zinc chloride to give resin-bound imidazolylzinc chloride which was cross-coupled with aryl and heteroaryl iodides under palladium(0) catalysis. Cleavage using TFA-CH2Cl2 (1:1) at room temperature afforded 2-aryl/heteroaryl substituted 1-hydroxyimidazoles.

引用

页码：909 / 913

页数：5

共 34 条

[1] [Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23
[2] BAKES BJ, 1994, J AM CHEM SOC, V116, P11171
[3] Blettner CG, 1999, SYNLETT, P307
[4] Blettner CG, 1998, SYNLETT, P295
[5] Palladium-catalyzed coupling of functionalized bromoarenes to a polystyrene-bound aryl tributylstannane
Brody, MS
Finn, MG
[J]. TETRAHEDRON LETTERS, 1999, 40 (03) : 415 - 418
[6] Parallel synthesis of tamoxifen and derivatives on solid support via resin capture
Brown, SD
Armstrong, RW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7076 - 7077
[7] Synthesis of tetrasubstituted ethylenes on solid support via resin capture
Brown, SD
Armstrong, RW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) : 6331 - 6332
[8] DESICCANT EFFICIENCY IN SOLVENT DRYING .3. DIPOLAR APROTIC-SOLVENTS
BURFIELD, DR
SMITHERS, RH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20) : 3966 - 3968
[9] 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
Chamoin, S
Houldsworth, S
Snieckus, V
[J]. TETRAHEDRON LETTERS, 1998, 39 (24) : 4175 - 4178
[10] 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
Chamoin, S
Houldsworth, S
Kruse, CG
Bakker, WI
Snieckus, V
[J]. TETRAHEDRON LETTERS, 1998, 39 (24) : 4179 - 4182

← 1 2 3 4 →