sodium carbonate; trans-PdBr(N-Succ)(PPh3)2 in tetrahydrofuran T=80°C; Suzuki-Miyaura cross-coupling; 4 h;

caesium carbonate; [(P{(C6H11)3})2Pd(Cl)2] in 1,4-dioxane; water T=115°C; Suzuki reaction; 24 h;

1: para-iodoanisole With n-butyllithium; zinc dibromide in tetrahydrofuran; hexane T=-78 - 20°C; 2: 2-iodo-2-cyclopent-2-en-1-one With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trifuran-2-yl-phosphane in N,N-dimethyl-formamide T=20°C; Negishi coupling; 5 h;

triphenyl-arsane; silver(l) oxide in tetrahydrofuran; water Inert atmosphere;

1: 78 percent / NaBr; oxone; Et3N / CH2Cl2; H2O / 5 h / 0 - 20 °C 2: 18 percent / Cs2CO3 / Pd(PCy3)2Cl2 / dioxane; H2O / 24 h / 115 °C View Scheme

1: para-iodoanisole With n-butyllithium; zinc dibromide in tetrahydrofuran; hexane T=-78 - 20°C; 2: 2-iodo-2-cyclopent-2-en-1-one With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; trifuran-2-yl-phosphane in N,N-dimethyl-formamide T=20°C; Negishi coupling; 5 h; Title compound not separated from byproducts;

Yield given. Multistep reaction;