Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald–Hartwig Amination
Tomoteru Mizusaki
1, 2, 3
,
Kazuhiro Matsumoto
1
,
Katsuhiko Takeuchi
1
,
Norihisa Fukaya
1
,
Yukio Takagi
3
,
Jun-Chul Choi
1, 2
3
N. E. CHEMCAT Corporation, 678 Ipponmatsu, Numazu, Shizuoka 410-0314, Japan
|
Publication type: Journal Article
Publication date: 2019-04-15
scimago Q2
wos Q1
SJR: 0.676
CiteScore: 5.1
Impact factor: 2.9
ISSN: 02767333, 15206041
Organic Chemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
An immobilized N-heterocyclic carbene (NHC)-Pd complex was prepared via direct silyl linker installation onto the imidazole backbone of commercially available 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr) ligand. The IPr backbone was lithiated and treated with Me2SiCl2 to afford ClMe2Si-IPr, which reacted with [Pd(π-allyl)Cl]2 to yield a ClMe2Si-IPr-Pd complex, and this was immobilized on Wang resin. The immobilized NHC-Pd complex facilitated quantitative Buchwald–Hartwig amination of aryl chlorides within 10 min, even at a low Pd loading of 0.2 mol %. The catalyst could be removed from the reaction mixture by simple filtration, and Pd leaching into the reaction medium was suppressed to below 1 ppm.
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17
Total citations:
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Citations from 2024:
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(35.3%)
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GOST
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Mizusaki T. et al. Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald–Hartwig Amination // Organometallics. 2019. Vol. 38. No. 9. pp. 1872-1876.
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Mizusaki T., Matsumoto K., Takeuchi K., Fukaya N., Takagi Y., Choi J. Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald–Hartwig Amination // Organometallics. 2019. Vol. 38. No. 9. pp. 1872-1876.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.organomet.9b00159
UR - https://doi.org/10.1021/acs.organomet.9b00159
TI - Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald–Hartwig Amination
T2 - Organometallics
AU - Mizusaki, Tomoteru
AU - Matsumoto, Kazuhiro
AU - Takeuchi, Katsuhiko
AU - Fukaya, Norihisa
AU - Takagi, Yukio
AU - Choi, Jun-Chul
PY - 2019
DA - 2019/04/15
PB - American Chemical Society (ACS)
SP - 1872-1876
IS - 9
VL - 38
SN - 0276-7333
SN - 1520-6041
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Mizusaki,
author = {Tomoteru Mizusaki and Kazuhiro Matsumoto and Katsuhiko Takeuchi and Norihisa Fukaya and Yukio Takagi and Jun-Chul Choi},
title = {Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald–Hartwig Amination},
journal = {Organometallics},
year = {2019},
volume = {38},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.organomet.9b00159},
number = {9},
pages = {1872--1876},
doi = {10.1021/acs.organomet.9b00159}
}
Cite this
MLA
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Mizusaki, Tomoteru, et al. “Direct Installation of a Silyl Linker on Ready-Made NHC Ligands: Immobilized NHC-Pd Complex for Buchwald–Hartwig Amination.” Organometallics, vol. 38, no. 9, Apr. 2019, pp. 1872-1876. https://doi.org/10.1021/acs.organomet.9b00159.