HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490935Generated: October 26, 2026
Benzamide → 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide
https://huagongshe.com/reaction/1490935
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzamide | HCID 2331 | — |
| Reagent | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reagent | 8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-one | HCID 164681385 | — |
| Catalyst | Bis(1,5-cyclooctadiene)dimethoxydiiridium | HCID 76001521 | — |
| Catalyst | Potassium tert-butoxide | HCID 86639980 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide | HCID 2760587 | 9% |
| Product | 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide | HCID 2760588 | 14% |
Reaction Steps
In an argon filled glove box, a 5.0 mL wheaton microreactor was charged with [Ir(cod)(OMe)]2 (1.98 mg, 1.5 mol%), L1 ligand (2.1 mg, 3.5 mol%), B2pin2 (50.8 mg, 1.0 equiv.), KOtBu (1.0 mg, 4.5 mol%), and dry THF (1.0 mL). The reaction mixture was stirred for 2 minutes at room temperature. To this mixture, benzamide (24.2 mg, 0.2 mmol) was added. The microreactor was capped with a teflon pressure cap and placed into pre-heated aluminum block at 80 oC. After 12 h, (judged by GC/MS), we found that the conversion was 23% and meta/para ratio was 1/1.5.
Provenance & Evidence
| DOI | 10.1002/anie.201809929 |
|---|
| Source dataset | Borylation dataset from Roche |
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| ORD ID | ord-8a61495c860141f1a8046698b9543528 |
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| Source note | Borylation dataset from Roche |
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