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Introduction of terminal alkynes into the 2-and 8-positions of the Troger's base core via Sonogashira reaction of 2,8-diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine

Jensen, Jacob LU ; Strozyk, Michal and Wärnmark, Kenneth LU (2002) In Synthesis p.2761-2765
Abstract
Conditions for the introduction of terminal alkynes into the 2- and 8-positions of the Troger's base core via Sonogashira reaction of 2,8-diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine were established. Only the use of the bulky and electron-rich phosphine P(t-Bu)(3) as a ligand for the palladium catalyst allowed for the Sonogashira reaction to proceed effectively. In addition, excessive equivalents of the alkyne were found to increase the yields of the coupling. The established optimal conditions for the introduction of terminal alkynes into the Troger's base core were applied to differently aryl- and pyridyl-substituted terminal alkynes to afford new analogues of Troger's base 3a-g in moderate to excellent yields.
Please use this url to cite or link to this publication:
author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
ligands, alkynes, Troger's base, Sonogashira reaction, supramolecular, chemistry
in
Synthesis
issue
18
pages
2761 - 2765
publisher
Oxford Polytechnic, Oxford
external identifiers
  • wos:000180052300017
ISSN
0039-7881
DOI
10.1055/s-2002-35989
language
English
LU publication?
yes
id
302a5878-e546-4b7a-bcfc-86c0ccf3d8d1 (old id 320518)
date added to LUP
2007-10-24 15:45:52
date last changed
2016-04-16 03:39:13
@article{302a5878-e546-4b7a-bcfc-86c0ccf3d8d1,
  abstract     = {Conditions for the introduction of terminal alkynes into the 2- and 8-positions of the Troger's base core via Sonogashira reaction of 2,8-diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine were established. Only the use of the bulky and electron-rich phosphine P(t-Bu)(3) as a ligand for the palladium catalyst allowed for the Sonogashira reaction to proceed effectively. In addition, excessive equivalents of the alkyne were found to increase the yields of the coupling. The established optimal conditions for the introduction of terminal alkynes into the Troger's base core were applied to differently aryl- and pyridyl-substituted terminal alkynes to afford new analogues of Troger's base 3a-g in moderate to excellent yields.},
  author       = {Jensen, Jacob and Strozyk, Michal and Wärnmark, Kenneth},
  issn         = {0039-7881},
  keyword      = {ligands,alkynes,Troger's base,Sonogashira reaction,supramolecular,chemistry},
  language     = {eng},
  number       = {18},
  pages        = {2761--2765},
  publisher    = {Oxford Polytechnic, Oxford},
  series       = {Synthesis},
  title        = {Introduction of terminal alkynes into the 2-and 8-positions of the Troger's base core via Sonogashira reaction of 2,8-diiodo-4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine},
  url          = {http://dx.doi.org/10.1055/s-2002-35989},
  year         = {2002},
}