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Cyclic Alkyne Approach to Heteroatom‐Containing Polycyclic Aromatic Hydrocarbon Scaffolds
Author(s) -
Darzi Evan R.,
Barber Joyann S.,
Garg Neil K.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903060
Subject(s) - pericyclic reaction , heteroatom , alkyne , aryne , chemistry , polycyclic aromatic hydrocarbon , cycloaddition , carbon fibers , hydrocarbon , organic chemistry , combinatorial chemistry , photochemistry , ring (chemistry) , catalysis , materials science , composite number , composite material
We report a modular synthetic strategy for accessing heteroatom‐containing polycyclic aromatic hydrocarbons (PAHs). Our approach relies on the controlled generation of transient heterocyclic alkynes and arynes. The strained intermediates undergo in situ trapping with readily accessible oxadiazinones. Four sequential pericyclic reactions occur, namely two Diels–Alder/retro‐Diels–Alder sequences, which can be performed in a stepwise or one‐pot fashion to assemble four new carbon–carbon (C−C) bonds. These studies underscore how the use of heterocyclic strained intermediates can be harnessed for the preparation of new organic materials.