HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490572Generated: October 30, 2026
1,3,5-Trimethoxybenzene → 4,4,5,5-Tetramethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborolane
https://huagongshe.com/reaction/1490572
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,3,5-Trimethoxybenzene | HCID 69301 | — |
| 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 | 4,4,5,5-Tetramethyl-2-(2,4,6-trimethoxyphenyl)-1,3,2-dioxaborolane | HCID 21923927 | 20% |
Reaction Steps
The general procedure A was followed using 1,3,5-trimethoxybenzene (84.1 mg, 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 150 oC. The 1H NMR conversion was 21%. 5af was obtained as white solid (30.1 mg, 20%) after purification by silica gel flash chromatography (EtOAc/PE=1:20 v/v). m.p.: 114-116 oC.
Provenance & Evidence
| DOI | 10.1021/jacs.5b05252 |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-3b44e04ef3134bc5ba0999b39d644837 |
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| Source note | Borylation dataset from Roche |
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