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Cycloaddition Cascades of Strained Alkynes and Oxadiazinones
Author(s) -
Ramirez Melissa,
Darzi Evan R.,
Donaldson Joyann S.,
Houk Kendall N.,
Garg Neil K.
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202105244
Subject(s) - pericyclic reaction , cycloaddition , tetracene , aryne , pentacene , chemistry , computational chemistry , cascade reaction , acene , combinatorial chemistry , photochemistry , nanotechnology , organic chemistry , molecule , anthracene , materials science , catalysis , thin film transistor , layer (electronics)
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.