HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490773Generated: October 29, 2026
HCID 102470805, compound → HCID 178431072, compound
https://huagongshe.com/reaction/1490773
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | HCID 102470805 | HCID 102470805 | — |
| 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 178431048 | HCID 178431048 | 11% |
| Product | HCID 178431072 | HCID 178431072 | 57% |
Reaction Steps
Following general procedure F using 4d (86 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 5.7:1 meta:para borylation in 85% yield (12% starting material remaining). The crude product was purified by silica gel chromatography (15% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 5.4:1 mixture of meta:para ratio, as determined by 1 H NMR) as a yellowish oil (79 mg, 0.17 mmol, 68%).
Provenance & Evidence
| DOI | 10.1002/anie.201708967 |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-b22003b7c65748a7a5209d4fd3292b64 |
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| Source note | Borylation dataset from Roche |
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