2-Methylacetophenone → 1-[2-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone

HRID 1490930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1490930
CC(=O)c1ccccc1C>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1C.CC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1C

Komponenten

7

Edukt 1

HCID 113402-Methylacetophenone

Produkt 2

HCID 754871961-[2-Methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanoneAusbeute 49 %HCID 1299466461-(2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-oneAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733548Bis(pinacolato)diboraneReagenzHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagenzHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumKatalysatorHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

General procedure Cwas applied to 1-(2’-methylphenyl)ethanone15f(54mg, 0.4mmol). The reaction mixture was was stirredat room temperature for 16hours giving a conversion of 87%(GC-MS) and 16fand 17fin a 56:44 mixture which also contained unreacted starting material 15f(1H NMRspectrum).

Quellen und Nachweise

ORD-Eintrag
ord-7774858fb93f41f7b91cc112210ae5ae
Quelldatensatz
Borylation dataset from Roche

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