Use of a recyclable poly(N-vinyl carbazole) palladium(II) complex catalyst: Heck cross-coupling reaction under phosphine-free and aerobic conditions

Abstract

A novel pathway for cross-coupling reaction of terminal alkenes with aryl halides (Heck cross-coupling) has been described using a new phosphine-free poly(Nvinyl carbazole) anchored palladium(II) complex as catalyst in aerobic conditions. The catalyst was found to be highly active for the couplings of a variety of substituted and non-substituted aryl halides with terminal alkenes and to smoothly afford the corresponding desired products in good to excellent yields. The catalyst can be reused at least six times without noticeable decrease in catalytic activity.

Efficient, Selective, and Recyclable Palladium Catalysts in Carbon−Carbon Coupling Reactions

“…The palladium content of the recovered catalyst decreased to 5.40 wt % after eight uses. Similar catalyst performance, that is, high yields in the coupling of iodo- and bromoarenes (76−100%) and high but decreasing yields in recycling (entry 6), have been observed with catalyst 12.8% Pd- 35 -PVCarb bearing a Pd 2+ complex anchored to functionalized poly( N -vinylcarbazole) with 0.5 ppm of leached Pd detected …”

Differential selectivity measurements and competitive reaction methods as effective means for mechanistic studies of complex catalytic reactions

“…[14][15][16][17] Nevertheless, several papers were published after 2006 (ref. [19][20][21][22][23][24][25][26][27][28][29] which questioned the homogeneous catalysis mechanism of the Mizoroki-Heck reaction, indicating the complexity in distinguishing the homogeneous and heterogeneous catalysis mechanisms once more. The catalytic mechanism of the Suzuki-Miyaura reaction is still debated.…”

Synthetic Routes to Fluorescent Dyes Exhibiting Large Stokes Shifts

“…21 Styrene was used in a Heck coupling using Pd(II) and K 2 CO 3 in benzene/DMF to afford compound 11. 22 The Zconformation of the double bond was confirmed by the 16.9 Hz proton−proton coupling constant. A Sonogashira crosscoupling reaction [Pd(PPh 3 ) 4 ] catalyst, triethylamine as base was used to insert a tolylacetylene residue.…”

“…Styrene was used in a Heck coupling using Pd(II) and K 2 CO 3 in benzene/DMF to afford compound 11 . The Z-conformation of the double bond was confirmed by the 16.9 Hz proton–proton coupling constant.…”