4-Phenylthioanisole → 4,4,5,5-Tetramethyl-2-[3-(4-methylsulfanylphenyl)phenyl]-1,3,2-dioxaborolane

HRID 1491141Notes

Reaction equation

HRID 1491141 reaction equation
CSc1ccc(-c2ccccc2)cc1>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]>CSc1ccc(-c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)cc1.CSc1ccc(-c2cccc(B3OC(C)(C)C(C)(C)O3)c2)cc1

Participants

7

Reactant 1

HCID 110198974-Phenylthioanisole

Product 2

HCID 1325102634,4,5,5-Tetramethyl-2-[3-(4-methylsulfanylphenyl)phenyl]-1,3,2-dioxaborolaneYield 54%HCID 1325102644,4,5,5-Tetramethyl-2-[4-(4-methylsulfanylphenyl)phenyl]-1,3,2-dioxaborolaneYield 29%

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 meta- and para-borylated products (135 mg, 83% yield, meta/para = 1.9); meta- and para-Isomers (5g+5gʹ) were obtained by further purification by GPC (119 mg, 73% yield), white solid (mp. 112-114 oC)

Sources & evidence

ORD record
ord-4474d4e5ec424758ae7a42fa7cc9671c
Source dataset
Borylation dataset from Roche

Reaction notes

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