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

doi:10.1039/d1cc01271a

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

Institute of Chemistry

The Hebrew University of Jerusalem

Research output: Contribution to journal › Article › peer-review

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 language	English
Article number	01271
Pages (from-to)	5342-5345
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	43
DOIs	https://doi.org/10.1039/d1cc01271a
State	Published - 28 May 2021

All Science Journal Classification (ASJC) codes

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d1cc01271a

Cite this

@article{a1459db3d3134cadb37ed739c183693d,

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

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.",

author = "Iris Berg and Lillian Hale and Mazal Carmiel-Kostan and Toste, {F. Dean} and Elad Gross",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2021",

month = may,

day = "28",

doi = "10.1039/d1cc01271a",

language = "الإنجليزيّة",

volume = "57",

pages = "5342--5345",

number = "43",

}

TY - JOUR

T1 - Using silyl protecting group to enable post-deposition C-C coupling reactions of alkyne-functionalized N-heterocyclic carbene monolayers on Au surfaces

AU - Berg, Iris

AU - Hale, Lillian

AU - Carmiel-Kostan, Mazal

AU - Toste, F. Dean

AU - Gross, Elad

N1 - Publisher Copyright: © The Royal Society of Chemistry.

PY - 2021/5/28

Y1 - 2021/5/28

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85106987032&partnerID=8YFLogxK

U2 - 10.1039/d1cc01271a

DO - 10.1039/d1cc01271a

M3 - مقالة

C2 - 33928978

SN - 1359-7345

VL - 57

SP - 5342

EP - 5345

JO - Chemical Communications

JF - Chemical Communications

IS - 43

M1 - 01271

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this