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Introduction of aromatic and heteroaromatic groups in the 2-and 8-positions of the Troger's base core by Suzuki, Stille and Negishi cross-coupling reactions - A comparative study

Solano, Carlos LU ; Svensson, Daniel; Olomi, Zarina LU ; Jensen, Jacob LU ; Wendt, Ola LU and Wärnmark, Kenneth LU (2005) In European Journal of Organic Chemistry 2005(16). p.3510-3517
Abstract
A comparative study on the bis(functionalization) of the Troger's base core by aromatic and heteroaromatic groups using palladium-catalyzed cross-coupling reactions is presented. Three different reactions, the Suzuki, Stille, and Negishi couplings, were investigated using Troger's base analogues equally substituted in the 2,8-positions with (HO)(2)B, Bu3Sn and ZnCl groups, respectively, as the metallated comportent. Six aryl halides with different electronic and steric properties were employed as coupling partners. The presence of the bulky and electron-rich phosphane P(tBu)(3) as cocatalyst was found to play an important role. In addition, the palladium source, [Pd(PPh3)(4)] or [Pd-2(dba)(3)], was also found to be all important factor for... (More)
A comparative study on the bis(functionalization) of the Troger's base core by aromatic and heteroaromatic groups using palladium-catalyzed cross-coupling reactions is presented. Three different reactions, the Suzuki, Stille, and Negishi couplings, were investigated using Troger's base analogues equally substituted in the 2,8-positions with (HO)(2)B, Bu3Sn and ZnCl groups, respectively, as the metallated comportent. Six aryl halides with different electronic and steric properties were employed as coupling partners. The presence of the bulky and electron-rich phosphane P(tBu)(3) as cocatalyst was found to play an important role. In addition, the palladium source, [Pd(PPh3)(4)] or [Pd-2(dba)(3)], was also found to be all important factor for the yield of the reactions, The Suzuki coupling was found to be the best method in general, giving excellent yields for most aryl halides, whereas the Stille and Negishi couplings gave moderate to good yields. Finally, the crystal structures of the 4-nitrophenyl- and the 2-pyridyl-appended analogues of Troger's base, 7d and 7f, are presented in the Supporting Information. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
European Journal of Organic Chemistry
volume
2005
issue
16
pages
3510 - 3517
publisher
John Wiley & Sons
external identifiers
  • wos:000231337000013
  • scopus:23944512482
ISSN
1434-193X
DOI
10.1002/ejoc.200500213
language
English
LU publication?
yes
id
6cea0111-c485-4971-b5ae-bfbf5c78628e (old id 152363)
date added to LUP
2007-07-10 14:35:27
date last changed
2017-08-27 04:25:21
@article{6cea0111-c485-4971-b5ae-bfbf5c78628e,
  abstract     = {A comparative study on the bis(functionalization) of the Troger's base core by aromatic and heteroaromatic groups using palladium-catalyzed cross-coupling reactions is presented. Three different reactions, the Suzuki, Stille, and Negishi couplings, were investigated using Troger's base analogues equally substituted in the 2,8-positions with (HO)(2)B, Bu3Sn and ZnCl groups, respectively, as the metallated comportent. Six aryl halides with different electronic and steric properties were employed as coupling partners. The presence of the bulky and electron-rich phosphane P(tBu)(3) as cocatalyst was found to play an important role. In addition, the palladium source, [Pd(PPh3)(4)] or [Pd-2(dba)(3)], was also found to be all important factor for the yield of the reactions, The Suzuki coupling was found to be the best method in general, giving excellent yields for most aryl halides, whereas the Stille and Negishi couplings gave moderate to good yields. Finally, the crystal structures of the 4-nitrophenyl- and the 2-pyridyl-appended analogues of Troger's base, 7d and 7f, are presented in the Supporting Information.},
  author       = {Solano, Carlos and Svensson, Daniel and Olomi, Zarina and Jensen, Jacob and Wendt, Ola and Wärnmark, Kenneth},
  issn         = {1434-193X},
  language     = {eng},
  number       = {16},
  pages        = {3510--3517},
  publisher    = {John Wiley & Sons},
  series       = {European Journal of Organic Chemistry},
  title        = {Introduction of aromatic and heteroaromatic groups in the 2-and 8-positions of the Troger's base core by Suzuki, Stille and Negishi cross-coupling reactions - A comparative study},
  url          = {http://dx.doi.org/10.1002/ejoc.200500213},
  volume       = {2005},
  year         = {2005},
}