HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490547Generated: October 31, 2026
1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- → N1,N1,N3,N3-Tetramethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzenediamine
https://huagongshe.com/reaction/1490547
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,3-Benzenediamine, N1,N1,N3,N3-tetramethyl- | HCID 89715 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | 3-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaborole | HCID 122380799 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Solvent | Cyclopentyl methyl ether | HCID 138539 | — |
| Product | N1,N1,N3,N3-Tetramethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzenediamine | HCID 20775197 | 93% |
Reaction Steps
The general procedure A was followed using N1 ,N1 ,N3 ,N3 -tetramethylbenzene-1,3-diamine (84 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 24 hours at 100 oC. 5b was obtained as white solid (135.2 mg, 93%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v). m.p.: 178-180 °C.
Provenance & Evidence
| DOI | 10.1021/jacs.5b05252 |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-dcac225a30e24bb3ae1171b013e2207a |
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| Source note | Borylation dataset from Roche |
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