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Synthesis of Cyclopenta‐HBCs and their Regioselective Chlorination During Oxidative Cyclodehydrogenation
Author(s) -
Hall Thomas B. J.,
Hoggard Bryce R.,
Larsen Christopher B.,
Lucas Nigel T.
Publication year - 2019
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201801812
Subject(s) - regioselectivity , chemistry , halogenation , electrophile , oxidative phosphorylation , ring (chemistry) , oxidative coupling of methane , medicinal chemistry , adduct , catalysis , organic chemistry , biochemistry
Hexa‐ peri ‐hexabenzocoronenes with a bay‐fused five‐membered ring are synthesized from fluorenyl precursors. The key oxidative cyclodehydrogenation step is accompanied by regioselective chlorination that is enhanced by methylation at the cyclopenta‐ring or increased reaction concentration. The CpHBC products undergo mild electrophilic aromatic bromination, without catalyst, to afford adducts suitable for π ‐extension by cross‐coupling.