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Pd‐Catalyzed Annulation of 1‐Halo‐8‐arylnaphthalenes and Alkynes Leading to Heptagon‐Embedded Aromatic Systems
Author(s) -
Yan Jianming,
Rahman Md. Shafiqur,
Yoshikai Naohiko
Publication year - 2019
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.201805746
Subject(s) - annulation , fluoranthene , catalysis , chemistry , naphthalene , palladium , medicinal chemistry , organic chemistry , pyrene
A palladium‐catalyzed heptagon‐forming annulation reaction between 1‐halo‐8‐arylnaphthalene and diarylacetylene is reported. The reaction is promoted using a catalytic system comprised of Pd(OAc) 2 , moderately electron‐deficient triarylphosphine P(4‐ClC 6 H 4 ) 3 , and Ag 2 CO 3 to afford benzo[4,5]cyclohepta[1,2,3‐ de ]naphthalene derivatives in moderate to good yields, in preference to fluoranthene as a competing byproduct. Twofold annulation can also be achieved to access a novel heptagon‐embedded polycyclic aromatic hydrocarbon compound.