3-(Methylsulfanyl)benzonitrile → HCID 177677472, compound

HRID 1491165Notes

Reaction equation

HRID 1491165 reaction equation
CSc1cccc(C#N)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.Cc1ccnc(-c2cc(C)ccn2)c1.[Ir].[Ir]>CSc1cc(C#N)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 130328133-(Methylsulfanyl)benzonitrile

Product 1

HCID 177677472HCID 177677472, compoundYield 82%

Reagents, catalysts & solvents 4

HCID 143384,4'-Dimethyl-2,2'-bipyridineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

dtbpy: A mixture of ortho- and meta-borylated products (112 mg, 82% yield, ortho/meta + para = <0.01); meta-Isomer 5s was obtained by further purification of the crude mixture by GPC (67 mg, 60% yield), white solid (mp. 75-77 oC);

Sources & evidence

ORD record
ord-0dc5c76273764473a9c47b34bf982241
Source dataset
Borylation dataset from Roche

Reaction notes

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