2-Bromothiophene → 2-(5-Bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1490563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490563
Brc1cccs1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC1CCCC1.C[OH2+].C[OH2+].[Ir].[Ir].c1ccc(N2B(B3Nc4ccccc4N3c3ccccn3)Nc3ccccc32)nc1>CC1(C)OB(c2ccc(Br)s2)OC1(C)C

Komponenten

6

Edukt 1

HCID 138512-Bromothiophene

Produkt 1

HCID 117377972-(5-Bromothiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733548Bis(pinacolato)diboraneReagenzHCID 1223807993-pyridin-2-yl-2-(3-pyridin-2-yl-1H-1,3,2-benzodiazaborol-2-yl)-1H-1,3,2-benzodiazaboroleReagenzHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumKatalysatorHCID 138539Cyclopentyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The general procedure A was followed using 2-bromothiophene (48.4 uL, 0.5 mmol) and B2pin2 (126.9 mg, 0.5 mmol, 1.0 eq.) as starting material. The resulting mixture was allowed to stir 16 hours at 100 oC. 5t was obtained as orange oil (138.7 mg, 96 %) after purification by silica gel flash chromatography (EtOAc/PE=1:40 v/v);

Quellen und Nachweise

ORD-Eintrag
ord-36a20897034c441f9bf4fb79b7aa05c4
Quelldatensatz
Borylation dataset from Roche

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