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Aryne-PAH-MS-ChemRXiv.pdf (4.16 MB)

Cyclic Alkyne Approach to Heteroatom-Containing Polycyclic Aromatic Hydrocarbon Scaffolds

preprint
submitted on 22.01.2019, 05:37 and posted on 22.01.2019, 15:40 by Evan Darzi, Joyann Barber, Neil Garg
We report a modular synthetic strategy for accessing heteroatom-containing polycyclic aromatic hydrocarbons (PAHs) that 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.

Funding

R01 GM123299

F32-GM122245

5T32GM008496

CHE-1048804

S10RR025631

History

Email Address of Submitting Author

neilgarg@chem.ucla.edu

Institution

University of California, Los Angeles

Country

United States

ORCID For Submitting Author

0000-0002-7793-2629

Declaration of Conflict of Interest

The authors have no conflicts of interest to declare.

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