TY - JOUR
T1 - Synthesis of an NHC-Coordinated Dialkyldisilavinylidene and Its Oxidation Providing a Silicon Analog of an Acetolactone
AU - Kobayashi, Ryo
AU - Ishida, Shintaro
AU - Iwamoto, Takeaki
N1 - Funding Information:
This work was supported by a JSPS KAKENHI grant JP20K21185 (T.I.) and the Division for Interdisciplinary Advanced Research and Education (DIARE) Tohoku University (R.K.). We thank Dr. Kenji Yoza (Bruker Japan) and Dr. Eunsang Kwon (Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University) for XRD analysis.
Publisher Copyright:
©
PY - 2021/4/12
Y1 - 2021/4/12
N2 - Although isolable silicon analogs of acetylene have been extensively studied, the silicon analogs of vinylidene, which is a short-lived isomer of acetylene, remain scarce. Herein, we report isolable NHC-coordinated dialkyldisilavinylidene 1 synthesized by the reduction of a tetrabromodisilane featuring a bulky alkyl protecting group. 1 was fully characterized by a combination of multinuclear NMR spectroscopy, high-resolution mass spectrometry, elemental analysis, and X-ray diffraction analysis. The UV-vis spectrum and DFT calculations disclosed that 1 possesses an SiaSi double bond and lone pair electrons on the terminal Si atom coordinated by the NHC. 1 reacted with N2O and B(C6F5)3 to provide a silicon analog of an acetolactone stabilized by a Lewis base and a Lewis acid (4).
AB - Although isolable silicon analogs of acetylene have been extensively studied, the silicon analogs of vinylidene, which is a short-lived isomer of acetylene, remain scarce. Herein, we report isolable NHC-coordinated dialkyldisilavinylidene 1 synthesized by the reduction of a tetrabromodisilane featuring a bulky alkyl protecting group. 1 was fully characterized by a combination of multinuclear NMR spectroscopy, high-resolution mass spectrometry, elemental analysis, and X-ray diffraction analysis. The UV-vis spectrum and DFT calculations disclosed that 1 possesses an SiaSi double bond and lone pair electrons on the terminal Si atom coordinated by the NHC. 1 reacted with N2O and B(C6F5)3 to provide a silicon analog of an acetolactone stabilized by a Lewis base and a Lewis acid (4).
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U2 - 10.1021/acs.organomet.1c00130
DO - 10.1021/acs.organomet.1c00130
M3 - Article
AN - SCOPUS:85104924033
SN - 0276-7333
VL - 40
SP - 843
EP - 847
JO - Organometallics
JF - Organometallics
IS - 7
ER -