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Abstract

Chemistry

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published: August 17th, 2018

DOI:

10.3791/58281

1Department of Chemistry and Biochemistry, University of Toledo, 2School of Green Chemistry and Engineering, University of Toledo

* These authors contributed equally

Abstract

Herein is presented a general strategy to perform reactions under mild to moderate CO2 pressures with dry ice. This technique obviates the need for specialized equipment to achieve modest pressures, and can even be used to achieve higher pressures in more specialized equipment and sturdier reaction vessels. At the end of the reaction, the vials can be easily depressurized by opening at room temperature. In the present example CO2 serves as both a putative directing group as well as a way to passivate amine substrates, thereby preventing oxidation during the organometallic reaction. In addition to being easily added, the directing group is also removed under vacuum, obviating the need for extensive purification to remove the directing group. This strategy allows the facile γ-C(sp3)-H arylation of aliphatic amines and has the potential to be applied to a variety of other amine-based reactions.

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Keywords Dry Ice

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