Cyclic Alkyne Approach to Heteroatom‐Containing Polycyclic Aromatic Hydrocarbon Scaffolds

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-07, Vol.58 (28), p.9419-9424
Main Authors: Darzi, Evan R., Barber, Joyann S., Garg, Neil K.
Format: Article
Language:English
Subjects:
Alkynes
arynes
Carbon
cyclic alkynes
cycloadditions
heterocycles
Intermediates
materials science
Organic materials
Polycyclic aromatic hydrocarbons
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Summary: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. A strained‐alkyne approach to access heteroatom‐rich polycyclic aromatic hydrocarbons is reported. This versatile synthetic platform allows for mild access to non‐symmetric tricyclic cores through a sequential or one‐pot reaction between two different strained alkynes and an oxadiazinone. In addition, a rapid synthesis of a small molecule and polymeric donor–acceptor fluorophore is described.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201903060