HCID 178523285, compound → HCID 178431091, compound

Participants

Role	Name	HCID	Charge
Reactant	HCID 178523285	HCID 178523285	—
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 178431041	HCID 178431041	8%
Product	HCID 178431091	HCID 178431091	63%

Reaction Conditions

Temperature	25 °C

Reaction Steps

Following general procedure F using 2,2,2‐trifluoro‐N‐(3‐(pyridin‐2‐yl)propyl)acetamide (58.1 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 rt for 15 hours before cooling and the solvents removed. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 7.8:1 meta:para borylation in 71% yield. The crude product was unable to be purified by silica gel chromatography and was hence characterised from the crude mixture.

Provenance & Evidence

DOI	10.1002/anie.201708967
Source dataset	Borylation dataset from Roche
ORD ID	ord-f79b8ef401de4d298e3e84f06ee0cf1a
Source note	Borylation dataset from Roche