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

Iris Berg, Lillian Hale, Mazal Carmiel-Kostan, F. Dean Toste, Elad Gross*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

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.

Original languageAmerican English
Article number01271
Pages (from-to)5342-5345
Number of pages4
JournalChemical Communications
Volume57
Issue number43
DOIs
StatePublished - 28 May 2021

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

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