Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 39, Pages 11846-11850Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706346
Keywords
arenes; boranes; borylation; carbenes; polycycles
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Funding
- Alexander von Humboldt foundation
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Reaction of an N-heterocyclic carbene (NHC)-borenium ion with 9,10-distyrylanthracene forms four B-C bonds through two selective, tandem hydroboration-electrophilic C-H borylations to yield an isolable, crystallographically characterizable polycyclic diborenium ion as its [NTf2](-) salt (1). Dehydrogenation of 1 with TEMPO radical followed by acidic workup yields a 3,9-diboraperylene as its corresponding borinic acid (2). This sequence can be performed in one pot to allow the facile, metal-free conversion of an alkene into a small molecule containing a boron-doped graphene substructure. Doubly boron-doped perylene 2 exhibits visible range absorbance and fluorescence in chloroform solution (phi=0.63) and undergoes two reversible one-electron reductions at moderate potentials of -1.30 and -1.64eV vs. ferrocenium/ferrocene in DMSO. Despite sterically accessible boron centers and facile electrochemical reductions, compound 2 is air-, moisture-, and silica gel-stable.
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