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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490805Generated: November 2, 2026

HCID 87773155, compound → HCID 178488279, compound

https://huagongshe.com/reaction/1490805

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHCID 87773155HCID 87773155—
ReagentBis(pinacolato)diboraneHCID 2733548—
ReagentTetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateHCID 165587889—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178486936HCID 17848693628%
ProductHCID 178488279HCID 17848827936%

Reaction Conditions

Temperature70 °C

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(2‐methoxyphenyl)propyl)acetamide (65.3 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). The reaction was stirred at 70 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 1.3:1 meta:para borylation in 65% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (19:1‐9:1) to give the title compound (as a 1.3:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (61.7 mg, 0.16 mmol, 64%).

Provenance & Evidence

DOI10.1002/anie.201708967
Source datasetBorylation dataset from Roche
ORD IDord-cefc16793bd1428e8bb5f39e767fd809
Source noteBorylation dataset from Roche