2-Methylbenzonitrile → 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

HRID 1490931Notes

Reaction equation

HRID 1490931 reaction equation
Cc1ccccc1C#N>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]>Cc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C#N.Cc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C#N

Participants

7

Reactant 1

HCID 107212-Methylbenzonitrile

Product 2

HCID 451585202-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileYield 52%HCID 532167692-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileYield 40%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

General procedure C was applied to 2-methylbenzonitrile 15g(47mg, 0.4mmol). The reaction mixture was stirredat room temperature for 16hours giving a conversion of >99% (GCMS) and 16g, 17gand 18in a 52:40:8 mixture (1H NMR spectrum).

Sources & evidence

ORD record
ord-88cb193daa5046a39bc40e3f108fe721
Source dataset
Borylation dataset from Roche

Reaction notes

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