Journal
ORGANIC LETTERS
Volume 13, Issue 10, Pages 2532-2535Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol2004534
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Funding
- MEXT, Japan [21685011, 21108510]
- Nagoya University
- Asahi Glass Foundation
- Grants-in-Aid for Scientific Research [21108510, 22750036, 21685011] Funding Source: KAKEN
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Treatment of perylene bisimides (PBIs) with bls(pinacolato)diboron in the presence of an iridium catalyst provides tetraborylated PBIs at 2,5,8,11-positions in good yields with perfect regioselectivity. The planar structure of the perylene core has been confirmed by X-ray diffraction analysis. Oxidation of tetraborylated PBI with hydroxylamine hydrochloride affords tetrahydroxy PBI In excellent yield, which exhibits a substantially blue-shifted absorption spectrum due to an Intramolecular hydrogenbonding interaction between carbonyl and hydroxy groups.
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