Issue 22, 2019

Mechanochemistry allows carrying out sensitive organometallic reactions in air: glove-box-and-Schlenk-line-free synthesis of oxidative addition complexes from aryl halides and palladium(0)

Abstract

Organic reactions that employ moisture- and/or oxygen-sensitive reagents or intermediates usually involve the use of glove-box or Schlenk-line techniques as well as dry and degassed solvents. Unfortunately, these requirements may greatly reduce the utility of the targeted organic molecules. Herein, we demonstrate that solvent-free mechanochemical synthetic techniques allow using highly oxygen-sensitive palladium(0) species in air for the stoichiometric oxidative addition of aryl halides. The low diffusion efficiency of gaseous oxygen in crystalline or amorphous solid-state reaction mixtures should be the main reason for the low impact of the presence of atmospheric oxygen on the sensitive oxidative addition reactions under the applied conditions. This study thus illustrates the outstanding potential of mechanochemistry to serve as an operationally simple, glove-box-and-Schlenk-line-free synthetic route to organometallic compounds and other valuable synthetic targets, even when sensitive reagents or intermediates are involved.

Graphical abstract: Mechanochemistry allows carrying out sensitive organometallic reactions in air: glove-box-and-Schlenk-line-free synthesis of oxidative addition complexes from aryl halides and palladium(0)

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Apr. 2019
Accepted
03 Maijs 2019
First published
07 Maijs 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 5837-5842

Mechanochemistry allows carrying out sensitive organometallic reactions in air: glove-box-and-Schlenk-line-free synthesis of oxidative addition complexes from aryl halides and palladium(0)

K. Kubota, R. Takahashi and H. Ito, Chem. Sci., 2019, 10, 5837 DOI: 10.1039/C9SC01711A

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