HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490805Generated: November 2, 2026
HCID 87773155, compound → HCID 178488279, compound
https://huagongshe.com/reaction/1490805
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | HCID 87773155 | HCID 87773155 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonate | HCID 165587889 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178486936 | HCID 178486936 | 28% |
| Product | HCID 178488279 | HCID 178488279 | 36% |
Reaction Steps
Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(2‐methoxyphenyl)propyl)acetamide (65.3 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 70 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.3:1 meta:para borylation in 65% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound (as a 1.3:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (61.7 mg, 0.16 mmol, 64%).
Provenance & Evidence
| DOI | 10.1002/anie.201708967 |
|---|
| Source dataset | Borylation dataset from Roche |
|---|
| ORD ID | ord-cefc16793bd1428e8bb5f39e767fd809 |
|---|
| Source note | Borylation dataset from Roche |
|---|