Cycloaddition Cascades of Strained Alkynes and Oxadiazinones.
Angew Chem Int Ed Engl
; 60(33): 18201-18208, 2021 Aug 09.
Article
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| MEDLINE
| ID: mdl-34080279
ABSTRACT
We report a computational and experimental study of the reaction of oxadiazinones and strained alkynes to give polycyclic aromatic hydrocarbons (PAHs). The reaction proceeds by way of a pericyclic reaction cascade and leads to the formation of four new carbon-carbon bonds. Using M06-2X DFT calculations, we interrogate several mechanistic aspects of the reaction, such as why the use of non-aromatic strained alkynes can be used to access unsymmetrical PAHs, whereas the use of arynes in the methodology leads to symmetrical PAHs. In addition, experimental studies enable the rapid synthesis of new PAHs, including tetracene and pentacene scaffolds. These studies not only provide fundamental insight regarding the aforementioned cycloaddition cascades and synthetic access to PAH scaffolds, but are also expected to enable the synthesis of new materials.
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MEDLINE
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En
Revista:
Angew Chem Int Ed Engl
Año:
2021
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Article
País de afiliación:
Estados Unidos