Ni(0) source Ligand Aryl halide Boronic acid Conditions Conversion(Aryl halide) Selectivity (product) Other 1 none Iodobenzene Phenylboronic acid r.t. 0 0 1 none Iodobenzene Phenylboronic acid UV, r.t. 0 0 1 none Iodobenzene Phenylboronic acid 100°C 60 100 1 none Iodobenzene Phenylboronic acid UV, 100°C 72 100 1 PPh3 Iodobenzene Phenylboronic acid UV, 100°C 47 100 1 dppe Iodobenzene Phenylboronic acid 100°C 22 100 1 dppe Iodobenzene Phenylboronic acid UV, 100°C 18 100 1 dppf Iodobenzene Phenylboronic acid 100°C 80 100 1 dppf Iodobenzene Phenylboronic acid UV 13 100 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 100 100 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 81 100 Addition COD (2:1) [Ni(COD)2] none Iodobenzene Phenylboronic acid UV, 100°C 15 100 [Ni(COD)2] PPh3 Iodobenzene Phenylboronic acid UV, 100°C 31 100 [Ni(COD)2] dppe Iodobenzene Phenylboronic acid UV, 100°C 20 100 [Ni(COD)2] dppf Iodobenzene Phenylboronic acid UV, 100°C 82 100 1 none Bromobenzene Phenylboronic acid UV, 100°C 82 100 1 PPh3 Bromobenzene Phenylboronic acid UV, 100°C 42 100 1 dppe Bromobenzene Phenylboronic acid UV, 100°C 0 100 1 dppf Bromobenzene Phenylboronic acid UV, 100°C 100 100 [Ni(COD)2] none Bromobenzene Phenylboronic acid UV, 100°C 0 100 [Ni(COD)2] PPh3 Bromobenzene Phenylboronic acid UV, 100°C 27 100 [Ni(COD)2] dppe Bromobenzene Phenylboronic acid UV, 100°C 0 100 [Ni(COD)2] dppf Bromobenzene Phenylboronic acid UV, 100°C 52 100 1 none Chloroanisole Phenylboronic acid UV, 100°C 21 63 1 PPh3 Chloroanisole Phenylboronic acid UV, 100°C 35 92 1 dppe Chloroanisole Phenylboronic acid UV, 100°C 0 0 1 dppf Chloroanisole Phenylboronic acid UV, 100°C 72 95 [Ni(COD)2] none Chloroanisole Phenylboronic acid UV, 100°C 0 0 [Ni(COD)2] PPh3 Chloroanisole Phenylboronic acid UV, 100°C 24 62 [Ni(COD)2] dppe Chloroanisole Phenylboronic acid UV, 100°C 0 0 [Ni(COD)2] dppf Chloroanisole Phenylboronic acid UV, 100°C 56 99 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 0 0 without base none dppf Iodobenzene Phenylboronic acid r.t. 0 0 none dppf Iodobenzene Phenylboronic acid UV, r.t. 0 0 none dppf Iodobenzene Phenylboronic acid 100°C 0 0 none dppf Iodobenzene Phenylboronic acid UV, 100°C 0 0 [Ni(COD)2] dppf Iodobenzene Phenylboronic acid r.t. 0 0 [Ni(COD)2] dppf Iodobenzene Phenylboronic acid UV, r.t. 0 0 [Ni(COD)2] dppf Iodobenzene Phenylboronic acid 100°C 61 100 1 dppf 2-Bromopyridine Phenylboronic acid UV, 100°C 72 82 1 dppf 4-Bromoacetophenone Phenylboronic acid UV, 100°C 82 99 1 dppf 2-Bromo-m-xylene Phenylboronic acid UV, 100°C 33 80 1 dppf Iodobenzene p-Tolylboronic acid UV, 100°C 100 99 1 dppf Iodobenzene 4-Chlorophenylboronic acid UV, 100°C 15 68 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 29 100 2.5 h reaction time 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 100 100 0.5 eq dct 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 75 100 1 eq dct 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 59 100 2 eq dct 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 35 100 4 eq dct 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 56 100 addition dct (2 eq) after 2.5 h 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 43 100 addition dct (2 eq) 1h prior to start 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 29 100 0.25 eq CS2 1 dppf Iodobenzene Phenylboronic acid UV, 100°C 15 100 2 eq CS2