HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490494Generated: October 27, 2026
N,N-dimethyl-m-toluidine → N,N,3-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine
https://huagongshe.com/reaction/1490494
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N,N-dimethyl-m-toluidine | HCID 8488 | — |
| Reagent | Pinacol | HCID 6425 | — |
| Reagent | Triethylamine | HCID 8471 | — |
| Reagent | Catecholborane | HCID 67506 | — |
| Catalyst | Tris(pentafluorophenyl)borane | HCID 582056 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | N,N,3-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine | HCID 66587807 | 75% |
Reaction Steps
Prepared from N,N,3-trimethylaniline (1e, 13.5 mg, 0.100 mmol, 1.00 equiv) and catBH (18.0 mg, 0.150 mmol, 1.50 equiv) according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3e (19.6 mg, 75%) as a white solid.
Provenance & Evidence
| DOI | 10.1002/anie.201611536 |
|---|
| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-c7114d160d51495cb17e79010eb2e33b |
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| Source note | Borylation dataset from Roche |
|---|
