HCID 3285659, compound → HCID 178486937, compound
Reaction equation
COc1ccccc1CCNC(=O)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]>COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1CCNC(=O)C(F)(F)F.COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1CCNC(=O)C(F)(F)FParticipants
7
Reactant 1
Product 2
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
Following general procedure F using 4j (61.8 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1:2.4 meta:para borylation in 85% yield. The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 1:2.3 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (76 mg, 0.2 mmol, 82%). By subtracting the resonances for the meta isomer, the NMR data of the para isomer can be assigned as follows:
Sources & evidence
- ORD record
- ord-85d4fd4cb3e14b03b8bd1a23d300cb71
- Source dataset
- Borylation dataset from Roche
Reaction notes
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