Synthesis 2021; 53(18): 3397-3403
special topic
Bond Activation – in Honor of Prof. Shinji Murai
Nickel-Catalyzed Homocoupling of Aryl Ethers with Magnesium Anthracene Reductant
Vishal Kumar Rawat
b
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
,
Kosuke Higashida∗
a
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo 001-0021, Japan
b
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
,
a
Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo 001-0021, Japan
b
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan
› Author Affiliations 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 calculation
Supporting 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
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
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