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. 2022 Mar 21;12(15):8833–8840. doi: 10.1039/d2ra00487a
graphic file with name d2ra00487a-u1.jpg
graphic file with name d2ra00487a-u2.jpg
Prod. X R1 Yield t (min) TON TOF
9a I NH2 85 120 180 90
9a Cl NH2 65 150 138 39
9b I OMe 92 70 195 168
9b Br OMe 90 110 191 104
9c I Me 85 90 180 120
9c Br Me 75 120 159 79
9c Cl Me 65 150 138 55
9d I H 95 15 202 808
9d Br H 95 20 202 612
9d Cl H 92 100 195 117
9e I CHO 93 60 197 197
9e Br CHO 85 85 180 128
9e Cl CHO 75 100 195 96
9f Br COMe 95 90 202 134
9g I NO2 94 25 200 487
9g Br NO2 90 35 191 330
9g Cl NO2 87 55 155 155
9h Br CN 80 90 170 113
9h Cl CN 60 180 148 49
a

Reaction conditions: phenylboronic acid (1.2 mmol), aryl halide (1.00 mmol), K2CO3 (Et3N when we used the aryl chlorides) (2.00 mmol), catalyst (0.007 g, 0.47 mol% of Pd), H2O (2.0 mL), 60 °C (90 °C when we used the aryl chlorides); all yields are isolated.