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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1490801Generated: October 29, 2026

HCID 178523288, compound → HCID 178431085, compound

https://huagongshe.com/reaction/1490801

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHCID 178523288HCID 178523288—
ReagentBis(pinacolato)diboraneHCID 2733548—
ReagentTetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonateHCID 165587889—
CatalystBis(1,5-cyclooctadiene)dimethoxydiiridiumHCID 76001521—
SolventTetrahydrofuranHCID 8028—
ProductHCID 178431085HCID 17843108569%
ProductHCID 178431088HCID 17843108812%

Reaction Conditions

Temperature35 °C

Reaction Steps

Following general procedure F using N‐(3‐(2,5‐difluorophenyl)propyl)‐2,2,2‐trifluoroacetamide (66.8 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 35 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 5.2:1 meta:para borylation in 99% 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 5.7:1 mixture of meta:para ratio, as determined by 1 H NMR) as a colourless oil (80.0 mg, 0.20 mmol, 81%).

Provenance & Evidence

DOI10.1002/anie.201708967
Source datasetBorylation dataset from Roche
ORD IDord-ed8829a9fb2540258ad7d264a7406e6b
Source noteBorylation dataset from Roche