Utilization of a copper-catalyzed diaryl ether synthesis for the preparation of verbenachalcone

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

“…An alternative disconnection using a 2-bromoanisole derivative as the electrophile failed. [81] Snieckus and co-workers elegantly used a directed ortho and remote metalation concept to prepare a series of 1,2,3-contiguous aromatic substitution patterns for compounds of type 198 [Eq. (29)].…”

Total synthesis, antiprotozoal and cytotoxicity activities of rhuschalcone VI and analogs

“…As far as we are aware, rhuschalcone VI (1) is the first and unique example of a natural dimer in which two chalcones are linked by a C-C bond; and no group has reported the total synthesis of C-C AB bichalcones. It is remarkable that whereas (a) the total synthesis of the bi-aryl ether-type bichalcones (rhuschalcones and verbenachalcone) have been reported, 1,3,4 by employing a novel application of the Ullmann synthesis and through anodic oxidation, respectively, and (b) a 0968-0896/$ -see front matter Ó 2010 Elsevier Ltd. All rights reserved. doi:10.1016/j.bmc.2010.02.055 number of flavonoids have been employed in Suzuki reactions, 5 the use of chalcones and the synthesis of any bi-aryl type rhus bichalcones has not yet been reported.…”

Renaissance of Ullmann and Goldberg Reactions - Progress in Copper Catalyzed C-N-, C-O- and C-S-Coupling

“…PhH and Cs 2 CO 3 (1 equiv) as the base in pyridine (24 h, 110°C) (Scheme 16). 48 It can be concluded from these results that copper-catalyzed coupling reactions offer access to a broad range of diaryl and arylalkyl ethers. Various copper salts proved to be useful catalyst precursors.…”