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A stable silylborane with diminished boron Lewis acidity.
Hiroto Yoshida1, Yuki Izumi1, Yuta Hiraoka1
1Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 739-8526, Japan. yhiroto@hiroshima-u.ac.jp.
Dalton Transactions (Cambridge, England : 2003)
|April 21, 2022
Summary
A novel silylborane, PhMe2Si-B(dan), was synthesized and found to be air-stable due to reduced Lewis acidity. This compound shows potential in catalytic silylboration and silylation reactions with alkynes.
Area of Science:
- Organosilicon Chemistry
- Organoboron Chemistry
- Catalysis
Background:
- Boron compounds often exhibit Lewis acidity, leading to sensitivity to air and moisture.
- Naphthalene-1,8-diaminato (dan) ligands can modulate the electronic properties of boron centers.
Purpose of the Study:
- To synthesize a novel dimethyl(phenyl)silylborane derivative with a naphthalene-1,8-diaminato substituent.
- To investigate the stability and synthetic utility of the new silylborane.
Main Methods:
- Synthesis of PhMe2Si-B(dan) via established organometallic procedures.
- Characterization of the synthesized compound using spectroscopic techniques.
- Evaluation of its reactivity in catalytic silylation and silylboration of alkynes.
Main Results:
- Successful synthesis of the air-stable dimethyl(phenyl)silylborane, PhMe2Si-B(dan).
- Demonstrated diminished Lewis acidity of the boron center due to the dan substituent.
- Showcased the compound's efficacy in catalyzing silylboration and silylation of alkynes.
Conclusions:
- The naphthalene-1,8-diaminato substituent effectively stabilizes the silylborane against air.
- PhMe2Si-B(dan) represents a valuable new reagent for catalytic transformations involving alkynes.
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