HCID 3869638, compound → HCID 178427431, compound

Participants

Role	Name	HCID	Charge
Reactant	HCID 3869638	HCID 3869638	—
Reagent	Bis(pinacolato)diborane	HCID 2733548	—
Reagent	4,4'-Di-tert-butyl-2,2'-bipyridyl	HCID 4249187	—
Catalyst	Bis(1,5-cyclooctadiene)dimethoxydiiridium	HCID 76001521	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 178427430	HCID 178427430	28%
Product	HCID 178427431	HCID 178427431	56%

Reaction Conditions

Temperature	35 °C

Reaction Steps

Following general procedure F using 4‐methyl‐N‐(2‐(trifluoromethyl)benzyl)benzenesulfonamide (82.3 mg, 0.25 mmol), B2pin2 (95 mg, 0.375 mmol), [Ir(COD)OMe]2 (2.5 mg, 0.00375 mmol) and dtbpy (2.0 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 1:2 meta:para borylation in 84% yield. As the para isomer could be characterised from the reaction with 1a the product was not isolated.

Provenance & Evidence

DOI	10.1002/anie.201708967
Source dataset	Borylation dataset from Roche
ORD ID	ord-6981e13bd7c14dcc934ee4bdf61b853f
Source note	Borylation dataset from Roche