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Palladium-Catalyzed C–H Activation Taken to the Limit. Flattening an Aromatic Bowl by Total Arylation

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† Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States
§ Department of Chemistry, Graduate School of Science, Nagoya University, Nagoya 464-8602, Japan
[email protected]; [email protected]
Cite this: J. Am. Chem. Soc. 2012, 134, 38, 15664–15667
Publication Date (Web):September 14, 2012
https://doi.org/10.1021/ja306992k
Copyright © 2012 American Chemical Society
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Abstract

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All 10 C–H positions on the rim of corannulene can be arylated by repetitive palladium-catalyzed C–H activation. To relieve congestion among the 10 tightly packed aryl substituents in the product, the central corannulene adopts a nearly planar geometry.

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Experimental procedures for the synthesis, isolation, and purification of 2a–c; 1H NMR, 13C NMR, UV–vis absorption, fluorescence, and MALDI-TOF mass spectra for 2a–c; X-ray crystal structure for 2c; MALDI mass spectra showing over-phenylation of corannulene after multiple cycles; geometry and strain energy calculations for 2a, octaphenylnaphthalene, and decaphenylanthracene; bowl-to-bowl inversion barrier calculations for 2a. This material is available free of charge via the Internet at http://pubs.acs.org.

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