N-(2-chlorophenyl)acetamide

Conditions: temp:50.01; pressure:0.00; stir:

Procedure: Following general procedure F using 2‐chloroacetanilide (42.4 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and 1a (3.8 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internalstandard 1,2‐dimethoxyethane showed 1:1.1 meta:para borylation in 74% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐6:4) to give the title compound (as a 1:1.3:0.4 mixture of meta:para:SM ratio, as determined by 1 H NMR) as a colourless oil. NMR yields have been used for all comparisons.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with the analogous procedure described in example 1 using 1-Iodo-2-nitrobenzene (124 mg, 0.5 mmol) and N-(2-chlorophenyl)-acetamide (102 mg, 0.6 mmol) as starting materials to yield the title compound as a yellow solid (74 mg, 61%). 1H NMR (DMSO) δ 2.63 (s, 3 H), 7.34 (d, J=7.9 Hz, 1 H), 7.41 (t, J=7.9 Hz, 1 H), 7.48 (t, J=7.9 Hz, 1 H), 7.64 (d, J=8.6 Hz, 2 H), 7.82 (d, J=7.9 Hz, 1 H), 7.92 (d, J=8.6 Hz, 2 H). The title compound was prepared with the analogous procedure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared with the analogous procedure described in example 1 using 1-Iodo-2-nitrobenzene (124 mg, 0.5 mmol) and N-(2-chlorophenyl)-acetamide (102 mg, 0.6 mmol) as starting materials to yield the title compound as a yellow solid (74 mg, 61%). 1H NMR (DMSO) δ 2.63 (s, 3 H), 7.34 (d, J=7.9 Hz, 1 H), 7.41 (t, J=7.9 Hz, 1 H), 7.48 (t, J=7.9 Hz, 1 H), 7.64 (d, J=8.6 Hz, 2 H), 7.82 (d, J=7.9 Hz, 1 H), 7.92 (d, J=8.6 Hz, 2 H). The title compound was prepared with the analogous procedure