HCID 178453188, compound → HCID 178453130, compound

Participants

Role	Name	HCID	Charge
Reactant	HCID 178453188	HCID 178453188	—
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 178453130	HCID 178453130	78%
Product	HCID 178453140	HCID 178453140	9%

Reaction Conditions

Temperature	50 °C

Reaction Steps

Following general procedure F using 4c (72.3 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). Stirred in vial at 50 °C for 20 hours. Analysis of crude 1 H NMR using internal standard 1,2‐dimethoxyethane showed 8.3:1 meta:para borylation in 86% yield. The crude product was purified by silica gel chromatography (10% EtOAc in Petroleum Ether 40‐60 o C) gave the title compound (as a 8.8:1 mixture of meta:para ratio, as determined by 1 H NMR) as a white solid (91 mg, 0.22 mmol, 87%).

Provenance & Evidence

DOI	10.1002/anie.201708967
Source dataset	Borylation dataset from Roche
ORD ID	ord-8560e57c774e4b10a8c1ed3c01a1d144
Source note	Borylation dataset from Roche