5-methyl-2-furonitrile → 5-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbonitrile

HRID 1491465Notes

Reaction equation

HRID 1491465 reaction equation
Cc1ccc(C#N)o1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>Cc1cc(B2OC(C)(C)C(C)(C)O2)c(C#N)o1.Cc1oc(C#N)cc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 6421085-methyl-2-furonitrile

Product 2

HCID 534358805-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbonitrileYield 87%HCID 576338825-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-furancarbonitrileYield 10%

Reagents, catalysts & solvents 4

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Sources & evidence

ORD record
ord-f9903988db4b4e0a875a9cdb79762a6c
Source dataset
Borylation dataset from Roche

Reaction notes

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