HCID 178424224, compound → HCID 178423573, compound
Reaction equation
Cc1ccccc1CCCNC(=O)C(F)(F)F>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CCCC[N+](CCCC)(CCCC)CCCC.C[OH2+].C[OH2+].Cc1ccc(-c2ccc(CS(=O)(=O)[O-])cn2)nc1.[Ir].[Ir]>Cc1cc(B2OC(C)(C)C(C)(C)O2)ccc1CCCNC(=O)C(F)(F)F.Cc1ccc(B2OC(C)(C)C(C)(C)O2)cc1CCCNC(=O)C(F)(F)FParticipants
7
Reactant 1
Product 2
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(o‐tolyl)propyl)acetamide (61.3 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 internal standard 1,2‐dimethoxyethane showed 13.0:1 meta:para borylation in 86% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (91:1‐8:1) to give the title compound (as a 10.5:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (74.7 mg, 0.20 mmol, 81%).
Sources & evidence
- ORD record
- ord-42ef8ac73afc49c8ab08e8b8ef865d8b
- Source dataset
- Borylation dataset from Roche
Reaction notes
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