potassium phosphate; tri-tert-butyl phosphine; tris(dibenzylideneacetone)dipalladium (0) in ethylene glycol dimethyl ether T=100°C; 18 h;

1: 1-bromo-3-methyl-benzene; 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane With (.eta.(5)-indenyl)Ir(1,5-cyclooctadiene); 1,2-bis(dimethylphosphine)ethane T=150°C; 17 h; 2: aniline With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine in ethylene glycol dimethyl ether T=100°C; Buchwald-Hartwig coupling; 19 h;

1: 1-chloro-3-methylbenzene; 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane With 1,2-bis(dimethylphosphine)ethane; (.eta.(5)-indenyl)Ir(1,5-cyclooctadiene) T=150°C; 8 h; 2: aniline With potassium phosphate; tri-tert-butyl phosphine; tris(dibenzylideneacetone)dipalladium (0) in ethylene glycol dimethyl ether T=100°C; 19 h;

potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; 2-Ph2P-2'-(Me2N)biphenyl in ethylene glycol dimethyl ether T=100°C; Buchwald-Hartwig coupling; 96 h;

potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 2-Ph2P-2'-(Me2N)biphenyl in ethylene glycol dimethyl ether T=100°C; Buchwald-Hartwig coupling; 21 - 48 h;

potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; 2-Ph2P-2'-(Me2N)biphenyl in ethylene glycol dimethyl ether T=100°C; Buchwald-Hartwig coupling; 21 h;

1: 1,2-bis(dimethylphosphino)ethane / (η5-indenyl)(1,5-cyclooctadiene)iridium / 150 °C 2: 79 percent / anhydrous K3PO4; P(t-Bu)3 / Pd2(dba)3 / 1,2-dimethoxy-ethane / 18 h / 100 °C View Scheme

1: 1,2-bis(dimethylphosphino)ethane / (η5-indenyl)(1,5-cyclooctadiene)iridium / 150 °C 2: 79 percent / anhydrous K3PO4; P(t-Bu)3 / Pd2(dba)3 / 1,2-dimethoxy-ethane / 18 h / 100 °C View Scheme