Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
A Highly Active Catalyst for Huisgen 1,3-Dipolar Cycloadditions Based on the Tris(triazolyl)methanol-Cu(I) Structure
Date
2009-10-15
Author
Özçubukçu, Salih
JİMENO, Ciril
Pericas, Miquel A.
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
38
views
0
downloads
Cite This
A new tris(1-benzyl-1H-1,2,3-triazol-4-yl)methanol ligand 3 has been prepared by a triple Cu(I)-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC). Ligand 3 forms a stable complex with CuCl, which catalyzes the Huisgen 1,3-dipolar cycloaddition on water or under neat conditions. Low catalyst loadings, short reaction times at room temperature, and compatibility with free amino groups make 3-CuCl an outstanding catalyst for CuAAC.
Subject Keywords
Physical and Theoretical Chemistry
,
Organic Chemistry
,
Biochemistry
URI
https://hdl.handle.net/11511/40921
Journal
ORGANIC LETTERS
DOI
https://doi.org/10.1021/ol9018776
Collections
Department of Chemistry, Article
Suggestions
OpenMETU
Core
A new strategy for the synthesis of pyridines from N-propargylic beta-enaminothiones
Kelgokmen, Yilmaz; Zora, Metin (Royal Society of Chemistry (RSC), 2019-03-07)
A new method for the synthesis of 2,4,5-trisubstituted pyridines from N-propargylic beta-enaminothiones is reported. beta-Enaminothiones were prepared by thionation of the corresponding beta-enaminones with Lawesson's reagent. When treated with diisopropylamine in DMF at room temperature, N-propargylic beta-enaminothiones yielded 2,4,5-trisubstituted pyridines in moderate to high yields, along with small amounts of 2-methylene-2,3-dihydro-1,4-thiazepines. The reaction was found to be general for a broad ran...
New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions
Doğan, Özdemir; GARNER, Philip; BULUT, Adnan; Youngs, Wiley J.; PANZNER, Matthew (American Chemical Society (ACS), 2006-10-12)
A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.
A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy and alpha '-hydroxy-alpha-methoxy cyclic enones
Demir, Ayhan Sıtkı; Caliskan, Z; Aydin, AE; Bicer, I (Elsevier BV, 2006-03-06)
A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy and alpha'-hydroxy-alpha-methoxy cyclic enones starting from alpha-hydroxy cyclic enones is described. Protection of 1,2-diketones, manganese(III) acetate-mediated acetoxylation followed by enzyme-mediated hydrolysis of alpha'-acetoxy enones gives acetoxy enones 3a-d and hydroxy enones 4a-d with high enantiomeric excesses (up to 99%) and good yields. The transesterification of rac-4b in the presence of DMAP af...
A new and efficient chemoenzymatic route to both enantiomers of alpha '-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones
Demir, Ayhan Sıtkı; Findik, H; Kose, E (Elsevier BV, 2004-03-08)
A chemoenzymatic synthesis of both enantiomers of the pharmacologically interesting alpha'-acetoxy-alpha-methyl and gamma-hydroxy-alpha-methyl cyclic enones starting from alpha-methyl-beta-methoxy cyclic enones is reported. Manganese(Ill) acetate-mediated acetoxylation followed by the enzyme-mediated hydrolysis of alpha'-acetoxy enone provides acetoxy enones 1a and 2a and hydroxy enones 1b and 2b with high enantiomeric excesses in good yields. The reduction of the acetoxy and hydroxy enones furnished both e...
A novel one-pot synthesis of ferrocenyl-substituted 1,2,4-oxadiazoles
Zora, Metin; Kelgokmen, YILMAZ (Elsevier BV, 2014-06-01)
One-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles via the reaction between 3-ferrocenylpropynal and amidoximes is described. 3-Ferrocenylpropynal reacts with a variety of amidoximes in the presence of KOH in refluxing dioxane to afford a broad range of 5-ferrocenyl-1,2,4-oxadiazole derivatives. The reaction first produces the corresponding conjugate addition product which, upon cyclization and rearrangement, yields the targeted 1,2,4-oxadiazole. The reaction appears to be general for a diversity of amidox...
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
S. Özçubukçu, C. JİMENO, and M. A. Pericas, “A Highly Active Catalyst for Huisgen 1,3-Dipolar Cycloadditions Based on the Tris(triazolyl)methanol-Cu(I) Structure,”
ORGANIC LETTERS
, pp. 4680–4683, 2009, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40921.