Copper-catalyzed N-arylation of imidazoles and benzimidazoles

被引：268

作者：

Altman, Ryan A. ^{[1
]}

Koval, Erica D. ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 16期

关键词：

D O I：

10.1021/jo070807a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4,7-Dimethoxy-1,10-phenanthroline (L1c) was found to be an efficient ligand for the copper-catalyzed N-arylation of imidazoles and benzimidazoles with both aryl iodides and bromides under mild conditions. Further optimization of the system has revealed that the addition of poly(ethylene glycol) accelerates this reaction. A variety of hindered and functionalized imidazoles, benzimidazoles, and aryl halides were transformed in good to excellent yields. Heteroaryl halides were also coupled in moderate to good yields. We also present the results obtained from a series of coupling reactions, which directly compare the use of L1c with other recently reported ligands.

引用

页码：6190 / 6199

页数：10

共 68 条

[1] Key role of water for nucleophilic substitutions in phase-transfer-catalyzed processes: A mini-review
Albanese, D
Landini, D
Maia, A
Penso, M
[J]. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2001, 40 (11) : 2396 - 2401
[2] Synthetic approaches to sterically hindered N-arylimidazoles through copper-catalyzed coupling reactions
Alcalde, E
Dinarès, I
Rodríguez, S
de Miguel, CG
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (08) : 1637 - 1643
[3] 4,7-Dimethoxy-1,10-phenanthroline:: An excellent ligand for the Cu-catalyzed N-arylation of imidazoles
Altman, Ryan A.
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2006, 8 (13) : 2779 - 2782
[4] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles
Anderson, Kevin W.
Tundel, Rachel E.
Ikawa, Takashi
Altman, Ryan A.
Buchwald, Stephen L.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6523 - 6527
[5] The copper-catalyzed N-arylation of indoles
Antilla, JC
Klapars, A
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) : 11684 - 11688
[6] Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles
Antilla, JC
Baskin, JM
Barder, TE
Buchwald, SL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) : 5578 - 5587
[7] Catalytic amination of 5-iodouracil derivatives
Arterburn, JB
Pannala, M
Gonzalez, AM
[J]. TETRAHEDRON LETTERS, 2001, 42 (08) : 1475 - 1477
[8] Inhibitors of apoptosis in lymphocytes:: Synthesis and biological evaluation of compounds related to pifithrin-α
Barchéchath, SD
Tawatao, RI
Corr, M
Carson, DA
Cottam, HB
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (20) : 6409 - 6422
[9] Copper in cross-coupling reactions - The post-Ullmann chemistry
Beletskaya, IP
Cheprakov, AV
[J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2337 - 2364
[10] Imidazoquinoxaline Src-family kinase p56Lck inhibitors:: SAR, QSAR, and the discovery of (S)-N-(2-chloro-6-methylphenyl)-2-(3-methyl-1-piperazinyl)imidazo[1,5-a]pyrido[3,2-e]pyrazin-6-amine (BMS-279700) as a potent and orally active inhibitor with excellent in vivo antiinflammatory activity
Chen, P
Doweyko, AM
Norris, D
Gu, HH
Spergel, SH
Das, J
Moquin, RV
Lin, J
Wityak, J
Iwanowicz, EJ
McIntyre, KW
Shuster, DJ
Behnia, K
Chong, S
de Fex, H
Pang, SH
Pitt, S
Shen, DR
Thrall, S
Stanley, P
Kocy, OR
Witmer, MR
Kanner, SB
Schieven, GL
Barrish, JC
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (18) : 4517 - 4529

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