Presentation Type
Poster
Start Date
5-4-2022 11:00 AM
End Date
5-4-2022 1:00 PM
Subjects
Organic chemistry, synthesis
Advisor
David Stuart
Student Level
Doctoral
Abstract
Arynes are ephemeral molecules that are yet to be fully exploited in synthetic strategy because they are often challenging to access. These reactive intermediates participate in a myriad of reactions that conventional chemistry is incapable of, making them extremely useful for the synthesis of important molecules like pharmaceuticals and agrochemicals. While classical approaches for synthesizing arynes employ cheap starting material, extremely harsh reagents are necessary to generate the aryne. In contrast, methods that do not require harsh reaction conditions do require starting material that is exceedingly difficult to synthesize. To access arynes quickly and efficiently, the work described herein aims to use abundant starting material to synthesize arynes in the fewest steps possible and without the need for extensive purification. Aryl sulfonium salts can be accessed in a single step from simple arenes and will generate arynes under basic conditions making them an appealing aryne precursor that bridges the gap between the methods described previously.
Rights
© Copyright the author(s)
IN COPYRIGHT:
http://rightsstatements.org/vocab/InC/1.0/
This Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
DISCLAIMER:
The purpose of this statement is to help the public understand how this Item may be used. When there is a (non-standard) License or contract that governs re-use of the associated Item, this statement only summarizes the effects of some of its terms. It is not a License, and should not be used to license your Work. To license your own Work, use a License offered at https://creativecommons.org/
Persistent Identifier
https://archives.pdx.edu/ds/psu/37483
Included in
Simple Arenes as Aryne Synthetic Equivalents via Sulfonium Salt Intermediates
Arynes are ephemeral molecules that are yet to be fully exploited in synthetic strategy because they are often challenging to access. These reactive intermediates participate in a myriad of reactions that conventional chemistry is incapable of, making them extremely useful for the synthesis of important molecules like pharmaceuticals and agrochemicals. While classical approaches for synthesizing arynes employ cheap starting material, extremely harsh reagents are necessary to generate the aryne. In contrast, methods that do not require harsh reaction conditions do require starting material that is exceedingly difficult to synthesize. To access arynes quickly and efficiently, the work described herein aims to use abundant starting material to synthesize arynes in the fewest steps possible and without the need for extensive purification. Aryl sulfonium salts can be accessed in a single step from simple arenes and will generate arynes under basic conditions making them an appealing aryne precursor that bridges the gap between the methods described previously.