N,N-Dimethyl-3-(methylsulfanyl)aniline → N,N-dimethyl-3-methylsulfanyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

HRID 1491142

Reaktionsgleichung

Reaktionsgleichung von HRID 1491142
CSc1cccc(N(C)C)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.C[OH2+].C[OH2+].Cc1ccc(C)cc1.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>CSc1cc(N(C)C)ccc1B1OC(C)(C)C(C)(C)O1

Komponenten

6

Edukt 1

HCID 20403482N,N-Dimethyl-3-(methylsulfanyl)aniline

Produkt 1

HCID 132510266N,N-dimethyl-3-methylsulfanyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anilineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2733548Bis(pinacolato)diboraneReagenzHCID 1349566232-Pyridin-2-yl-5-[2-[4-(trifluoromethyl)-1,3,2-dioxaborolan-2-yl]phenyl]pyridineReagenzHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumKatalysatorHCID 7809P-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

Ligand 3f: A mixture of ortho- and meta-borylated products (111 mg, 76% yield, ortho/meta + para = >30); ortho-borylated product 4h was obtained by further purification by GPC (100 mg, 68% yield), yellow oil;

Quellen und Nachweise

ORD-Eintrag
ord-1cb889e2f933486bac022f3a0a595351
Quelldatensatz
Borylation dataset from Roche

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