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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)

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Title: 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)
Authors: Kubota, Koji Browse this author
Takahashi, Rina Browse this author
Ito, Hajime Browse this author →KAKEN DB
Issue Date: 14-Jun-2019
Publisher: Royal Society of Chemistry
Journal Title: Chemical science
Volume: 10
Issue: 22
Start Page: 5837
End Page: 5842
Publisher DOI: 10.1039/c9sc01711a
PMID: 31293773
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.
Rights: https://creativecommons.org/licenses/by-nc/3.0/
Type: article
URI: http://hdl.handle.net/2115/75291
Appears in Collections:化学反応創成研究拠点:ICReDD (Institute for Chemical Reaction Design and Discovery : ICReDD) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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