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Direct Arylation of meso ‐Formyl Porphyrin
Author(s) -
Tokuji Sumito,
Awane Hiroyuki,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201203742
Subject(s) - porphyrin , aryl , chemistry , combinatorial chemistry , catalysis , palladium , medicinal chemistry , photochemistry , organic chemistry , alkyl
Palladium‐catalyzed direct arylation of meso ‐formyl Ni II porphyrin with aryl bromides provided β‐monoarylated meso ‐formyl porphyrins. In spite of the existence of the meso ‐formyl group, the reactions proceeded regioselectively at the β‐position adjacent to the formyl group. β‐Arylated formyl porphyrin was converted to a tetraline‐fused porphyrin by reduction and subsequent acid‐catalyzed cyclization and to a meso‐ ‐ meso vinylene‐bridged diporphyrin by McMurry coupling (see scheme).