3,4-Dichlorobenzonitrile → 4,5-Dichloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

HRID 1491467Notes

Reaction equation

HRID 1491467 reaction equation
N#Cc1ccc(Cl)c(Cl)c1>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]>CC1(C)OB(c2cc(C#N)cc(Cl)c2Cl)OC1(C)C.CC1(C)OB(c2cc(Cl)c(Cl)cc2C#N)OC1(C)C

Participants

7

Reactant 1

HCID 810513,4-Dichlorobenzonitrile

Product 2

HCID 576338724,5-Dichloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileYield 72%HCID 57633898863868-40-0Yield 17%

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-502144bb24ec47d5a8090f4ed0dbd46e
Source dataset
Borylation dataset from Roche

Reaction notes

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