HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490799Generated: October 29, 2026
HCID 178497625, compound → HCID 178497422, compound
https://huagongshe.com/reaction/1490799
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | HCID 178497625 | HCID 178497625 | — |
| 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 178497023 | HCID 178497023 | 3% |
| Product | HCID 178497422 | HCID 178497422 | 70% |
Reaction Steps
Following general procedure F using methyl 2‐(3‐(2,2,2‐trifluoroacetamido)propyl)benzoate (57.9 mg, 0.20 mmol), B2pin2 (101 mg, 0.40 mmol), [Ir(COD)OMe]2 (2.0 mg, 0.0030 mmol) and 1a (3.0 mg, 0.0060 mmol) in THF (1.0 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 >20:1 meta:para borylation in 100% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1‐8‐1) to give the title compound (as a 20:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (60.3 mg, 0.145 mmol, 73%).
Provenance & Evidence
| DOI | 10.1002/anie.201708967 |
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| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-95f9d9d54cbb4a7cbe27d6e616c6127a |
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| Source note | Borylation dataset from Roche |
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