Journal
TETRAHEDRON LETTERS
Volume 55, Issue 17, Pages 2809-2812Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.03.055
Keywords
1,3-Dipolar cycloaddition; Mesoionic heterocycles; Benzyne; Pyridyne; Isoindole
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Funding
- Department of Education GAANN fellowship
- Donors of the Petroleum Research Fund (PRF)
- American Chemical Society
- Wyeth
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Arynes derived from silyltriflate precursors undergo a smooth 1,3-dipolar cycloaddition with munchnones to furnish isoindoles and azaisoindoles in moderate to high yields. Modification of the fluoride source, solvent, and temperature allows for the selective generation of either isoindoles or benzanthracenimines, the latter of which serve as precursors to polycyclic aromatic hydrocarbons. (C) 2014 Elsevier Ltd. All rights reserved.
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