Preparation of naphthalenes via Pd-catalyzed annulation of 5-(2-bromophenyl)pent-3-en-1-ynes under Suzuki-Miyaura coupling conditions
Journal
Journal of the Chinese Chemical Society
ISSN
0009-4536
2192-6549
Date Issued
2024-08-22
Author(s)
Abstract
Highly substituted naphthalene derivatives were prepared via palladium-catalyzed reaction of 5-(2-bromophenyl)pent-3-en-1-ynes with arylboronic acids. Typically, reaction of 3-bromo-4-(3-(4-chlorophenyl)-5-phenyl-1-(p-tolyl)pent-2-en-4-yn-1-yl)-N-methylaniline (1a) with PhB(OH)2 in the presence of Pd(PPh3)4 as the catalyst under basic conditions provided 8-benzhydryl-7-(4-chlorophenyl)-N-methyl-5-(p-tolyl)naphthalen-2-amine (2a) quantitatively. Overall, 19 new naphthalene compounds were obtained by this methodology and their structures were characterized by spectroscopic methods. In addition, crystal structure of 2j was determined to confirm the structural details. Reaction pathway leading to the desired product is also discussed.
Subjects
coupling
cyclization
enyne
naphthalene
palladium
Publisher
Wiley
Type
journal article