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Synthesis 2021; 53(18): 3397-3403
DOI: 10.1055/a-1509-5954
DOI: 10.1055/a-1509-5954
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant
This work was supported by JSPS KAKENHI (JP20K15268) in Grant-in-Aid for Young Scientists to K.H. and JP18H03906 in Grant-in-Aid for Scientific Research (A) to M.S. JICA is thanked for providing a scholarship to V.K.R. under the FRIENDSHIP project.
Abstract
Nickel-catalyzed reductive homocoupling of aryl ethers has been achieved with Mg(anthracene)(thf)3 as a readily available low-cost reductant. DFT calculations provided a rationale for the specific efficiency of the diorganomagnesium-type two-electron reducing agent. The calculations show that the dianionic anthracene-9,10-diyl ligand reduces the two aryl ether substrates, resulting in the homocoupling reaction through supply of electrons to the Ni-Mg bimetallic system to form organomagnesium nickel(0)-ate complexes, which cause two sequential C–O bond cleavage reactions. The calculations also showed cooperative actions of Lewis acidic magnesium atoms and electron-rich nickel atoms in the C–O cleavage reactions.
Key words
homocoupling - C–O bond activation - nickel catalyst - magnesium anthracene - DFT calculationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1509-5954.
- Supporting Information
Publication History
Received: 24 April 2021
Accepted after revision: 17 May 2021
Accepted Manuscript online:
17 May 2021
Article published online:
15 June 2021
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Recent reports on nickel-catalyzed homocoupling reactions:
Recent reports on palladium-catalyzed homocoupling reactions:
The chemical structure of 1 was discussed:
For a variety of chemical properties of 1, see:
For reducing ability of 1 toward organic compounds, see:
For reducing ability of 1 toward metal reagents, see:
Recent reports of Kumada–Tamao–Corriu-type coupling of aryl ethers: