N-Triisopropylsilylpyrrole → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole

Participants

Role	Name	HCID	Charge
Reactant	N-Triisopropylsilylpyrrole	HCID 145136	—
Reagent	Pinacol	HCID 6425	—
Reagent	Triethylamine	HCID 8471	—
Reagent	Norbornadiene	HCID 8473	—
Reagent	Catecholborane	HCID 67506	—
Catalyst	Tris(pentafluorophenyl)borane	HCID 582056	—
Solvent	Toluene	HCID 1140	—
Product	3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(tris(propan-2-yl)silyl)-1H-pyrrole	HCID 11450924	45%

Reaction Conditions

Temperature	25 °C

Reaction Steps

Prepared from N-(triisopropylsilyl)-1H-pyrrole (4g, 44.6 mg, 0.200 mmol, 1.00 equiv), catBH (48.0 mg, 0.400 mmol, 2.00 equiv), N,N,4-trimethylaniline (1f, 2.7 mg, 0.020 mmol, 0.10 equiv), norbornene (18.8 mg, 0.20 mmol, 1.00 equiv) and B(C6F5)3 (10.1 mg, 0.020 mmol, 0.10 equiv) according to GP 3. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 6g[S4] (31.0 mg, 45%) as a white solid.

Provenance & Evidence

DOI	10.1002/anie.201611536
Source dataset	Borylation dataset from Roche
ORD ID	ord-a17137a9aad6418aa78cfde7c8f2ee9d
Source note	Borylation dataset from Roche