O=C(NCc1ccccc1Cl)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2ccc(CNC(=O)C(F)(F)F)c(Cl)c2)OC1(C)C.CC1(C)OB(c2ccc(Cl)c(CNC(=O)C(F)(F)F)c2)OC1(C)CFollowing general procedure F using N‐(2‐chlorobenzyl)‐2,2,2‐trifluoroacetamide (59.4 mg, 0.25 mmol), B2pin2 (127 mg, 0.50 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 mg, 0.0075 mmol) in THF (1.25 mL). The reaction was stirred at 35 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 5:33:56 dimeta:meta:para borylation in 93% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 4:33:66 mixture of dimeta:meta:para ratio, as determined by 1 H NMR) as a colourless oil (64 mg, 0.18 mmol, 70%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:
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