3-Fluoro-N-trifluoroacetylbenzylamine → HCID 178431089, compound

Participants

Role	Name	HCID	Charge
Reactant	3-Fluoro-N-trifluoroacetylbenzylamine	HCID 62492148	—
Reagent	Bis(pinacolato)diborane	HCID 2733548	—
Reagent	Tetrabutylazanium {5'-methyl-[2,2'-bipyridin]-5-yl}methanesulfonate	HCID 165587889	—
Catalyst	Bis(1,5-cyclooctadiene)dimethoxydiiridium	HCID 76001521	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 178431062	HCID 178431062	4%
Product	HCID 178431089	HCID 178431089	65%

Reaction Conditions

Temperature	50 °C

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐fluorobenzyl)acetamide (55.3 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 50 °C for 20 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 16.8:1 meta:para borylation in 71% yield. The crude product was purified by silica gel chromatography (Pet. Ether (40‐60):EtOAc (9:1) to give the title compound as a white solid (60.5 mg, 0.17 mmol, 69%).

Provenance & Evidence

DOI	10.1002/anie.201708967
Source dataset	Borylation dataset from Roche
ORD ID	ord-52ac8efd4b6f42b8acff3233e061b612
Source note	Borylation dataset from Roche