Palladium/Phosphite or Phosphate Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes to Produce 1,4‐Diaryl‐1,3‐butadienes

Abstract

Abstract:The intermolecular oxidative coupling of arylboronic acids with internal alkynes efficiently proceeds in a 2:2 manner in the presence of palladium acetate, a triaryl phosphite or phosphate, and silver carbonate as catalyst, ligand, and oxidant, respectively, to produce the corresponding 1,4-diaryl-1,3-butadiene derivatives.

Zirconoarylation of alkynes through p-chloranil-promoted reductive elimination of arylzirconates

“…1,1,2,3,4,4-Hexaphenyl-1,3-butadiene ( 5 ) [ 62 ]: To the reaction mixture containing 4a , CuCl (1 mmol) and TCQ (2 mmol) were added. The reaction mixture was stirred for 12 h at room temperature and compound 5 was isolated in 43% yield.…”

Palladium-catalyzed synthesis of 1,2,3,4-tetraalkyl-1,4-diarylbutadienes by cross-coupling of zirconacyclopentadienes with aryl iodides

“…Satoh et al [14] demonstrated that the coupling reactions of aryl boronic acids with alkynes can be performed with palladium catalyst to give multiarylated butadienes. Miura et al [15] optimized the process to produce 1,4-diaryl-1,3-butadienes by adding triaryl phosphate, but the product yields were still moderate due to the facile deactivation of the palladium catalyst under the oxidative conditions. Based on the above, we propose that the combination of CuCl and palladium catalyst may promote the formation of two sp 2 C-sp 2 C ---A c c e p t e d M a n u s c r i p t bonds which will offer bis-arylated-1,3-butadienes.…”

Simple Modifications for the Facile Preparation of 1,1,2,3,4,4‐Hexaaryl‐1,3‐butadienes

“…Tetraarylethene is one of aggregation‐induced emission (AIE) active molecules which have shown numerous applications in biological probes and imaging, chemical sensing, optoelectronics, and stimuli‐response materials [22] . On the other hand, Miura and Satoh and coworkers developed the synthesis of 1,3‐butadiene derivatives from the reaction of internal alkynes with arylboronic acids ( Scheme 1 ,a ) [23,24] . Although AIE active 1,1,2,3,4,4‐hexaaryl‐1,3‐butadienes and their polymers have been also synthesized using Miura ’s method, [25–31] applications are limited probably because the reaction temperature is too high (120 °C) and because some 1,1,2,3,4,4‐hexaaryl‐1,3‐butadienes can easily be cyclized to produce 1,1,2,3,4‐pentaarylated dihydronaphthalenes [32] .…”