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
(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:
https://lup.lub.lu.se/record/320518
- author
- Jensen, Jacob LU ; Strozyk, Michal and Wärnmark, Kenneth LU
- organization
- publishing date
- 2002
- 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
- scopus:0036929778
- ISSN
- 0039-7881
- DOI
- 10.1055/s-2002-35989
- language
- English
- LU publication?
- yes
- additional info
- The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
- id
- 302a5878-e546-4b7a-bcfc-86c0ccf3d8d1 (old id 320518)
- date added to LUP
- 2016-04-01 15:59:06
- date last changed
- 2022-01-28 08:27:59
@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}}, keywords = {{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}}, doi = {{10.1055/s-2002-35989}}, year = {{2002}}, }