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Issue 43, 2021
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Using silyl protecting group to enable post-deposition C–C coupling reactions of alkyne-functionalized N-heterocyclic carbene monolayers on Au surfaces

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Abstract

N-Heterocyclic carbenes (NHCs) were functionalized with a triisopropylsilyl (TIPS)-protected alkyne group and self-assembled on Au films to enable post-deposition functionalization by C–C coupling reactions. The TIPS group efficiently protected the alkyne and prevented its deprotonation during surface-anchoring of NHC. Sonogashira C–C coupling reactions were performed on the Au film in high yield following removal of the TIPS group, demonstrating that post-deposition coupling reactions can be employed to widen the chemical scope of surface-anchored NHCs.

Graphical abstract: Using silyl protecting group to enable post-deposition C–C coupling reactions of alkyne-functionalized N-heterocyclic carbene monolayers on Au surfaces

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Article information


Submitted
09 Mar 2021
Accepted
21 Apr 2021
First published
30 Apr 2021

Chem. Commun., 2021,57, 5342-5345
Article type
Communication

Using silyl protecting group to enable post-deposition C–C coupling reactions of alkyne-functionalized N-heterocyclic carbene monolayers on Au surfaces

I. Berg, L. Hale, M. Carmiel-Kostan, F. D. Toste and E. Gross, Chem. Commun., 2021, 57, 5342
DOI: 10.1039/D1CC01271A

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