Catalytic and computational studies of N-Heterocyclic carbene or phosphine-containing Copper(I) complexes for the synthesis of 5-lodo-1,2,3-Triazoles
File(s)
Published version
Author(s)
Lal, Steven
Rzepa, Henry S
Diez-Gonzalez, Silvia
Type
Journal Article
Abstract
Two complementary catalytic systems are reported for the 1,3-dipolar cycloaddition of azides and iodoalkynes. These are based on two commercially available/readily available copper complexes, [CuCl(IPr)] or [CuI(PPh3)3], which are active at low metal loadings (PPh3 system) or in the absence of any other additive (IPr system). These systems were used for the first reported mechanistic studies on this particular reaction. An experimental/computational-DFT approach allowed to establish that (1) some iodoalkynes might be prone to dehalogenation under copper catalysis conditions and, more importantly, (2) two distinct mechanistic pathways are likely to be competitive with these catalysts, either through a copper(III) metallacycle or via direct π-activation of the starting iodoalkyne.
Date Issued
2014-07-03
Date Acceptance
2014-05-01
Citation
ACS Catalysis, 2014, 4 (7), pp.2274-2287
ISSN
2155-5435
Publisher
American Chemical Society
Start Page
2274
End Page
2287
Journal / Book Title
ACS Catalysis
Volume
4
Issue
7
Copyright Statement
© 2014 American Chemical Society. Published with CC-BY license.
License URL
Sponsor
Engineering & Physical Science Research Council (EPSRC)
Engineering & Physical Science Research Council (EPSRC)
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000338693100023&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Grant Number
EP/K030760/1
EP/K039946/1
Subjects
Science & Technology
Physical Sciences
Chemistry, Physical
Chemistry
azide
iodotriazole
copper
cycloaddition
click chemistry
AZIDE-ALKYNE CYCLOADDITION
1,3-DIPOLAR CYCLOADDITIONS
EFFICIENT CATALYSTS
TERTIARY PHOSPHINE
CLICK CHEMISTRY
ORGANIC AZIDES
LIGANDS
REACTIVITY
1,2,3-TRIAZOLES
MECHANISMS
Publication Status
Published
Date Publish Online
2014-05-29