HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490748Generated: October 26, 2026
2-Methoxybenzylamine, N-trifluoroacetyl- → HCID 178486938, compound
https://huagongshe.com/reaction/1490748
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Methoxybenzylamine, N-trifluoroacetyl- | HCID 62491258 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | 4,4'-Di-tert-butyl-2,2'-bipyridyl | HCID 4249187 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178486938 | HCID 178486938 | 39% |
| Product | HCID 178488281 | HCID 178488281 | 20% |
Reaction Steps
Following general procedure F using 2,2,2‐Trifluoro‐N‐(2‐methoxybenzyl)acetamide (58.3 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 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1:2 meta:para borylation in 70% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1) to give the title compound (as a 1:2 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (53.1 mg, 0.15 mmol, 59%).
Provenance & Evidence
| DOI | 10.1002/anie.201708967 |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-77a974ad7b754ffb94b6a3f6496ee1e6 |
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| Source note | Borylation dataset from Roche |
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