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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490799Generated: October 29, 2026

HCID 178497625, compound → HCID 178497422, compound

https://huagongshe.com/reaction/1490799

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHCID 178497625HCID 178497625—
ReagentBis(pinacolato)diboraneHCID 2733548—
ReagentTetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateHCID 165587889—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178497023HCID 1784970233%
ProductHCID 178497422HCID 17849742270%

Reaction Conditions

Temperature50 °C

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

DOI10.1002/anie.201708967
Source datasetBorylation dataset from Roche
ORD IDord-95f9d9d54cbb4a7cbe27d6e616c6127a
Source noteBorylation dataset from Roche