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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490773Generated: October 29, 2026

HCID 102470805, compound → HCID 178431072, compound

https://huagongshe.com/reaction/1490773

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHCID 102470805HCID 102470805—
ReagentBis(pinacolato)diboraneHCID 2733548—
ReagentTetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateHCID 165587889—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178431048HCID 17843104811%
ProductHCID 178431072HCID 17843107257%

Reaction Conditions

Temperature50 °C

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

DOI10.1002/anie.201708967
Source datasetBorylation dataset from Roche
ORD IDord-b22003b7c65748a7a5209d4fd3292b64
Source noteBorylation dataset from Roche