Synthesis 2021; 53(18): 3397-3403
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

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.

Supporting Information



Publication History

Received: 24 April 2021

Accepted after revision: 17 May 2021

Publication Date:
17 May 2021 (online)

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