Benzene, 1-methyl-4-(methylthio)- → 4,4,5,5-Tetramethyl-2-(5-methyl-2-(methylthio)phenyl)-1,3,2-dioxaborolane

HRID 1491135Notes

Reaction equation

HRID 1491135 reaction equation
CSc1ccc(C)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(C)c(B2OC(C)(C)C(C)(C)O2)c1.CSc1ccc(C)cc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 69334Benzene, 1-methyl-4-(methylthio)-

Product 2

HCID 1389836424,4,5,5-Tetramethyl-2-(5-methyl-2-(methylthio)phenyl)-1,3,2-dioxaborolaneYield 41%HCID 178503150HCID 178503150, compoundYield 20%

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 (79 mg, 61% yield, ortho/meta + para = 2.0); meta-Isomer 5d was obtained by further purification by GPC (18 mg, 14% yield), yellow solid (mp. 85-87 oC)

Sources & evidence

ORD record
ord-8ab19278bad6421ab2de79245143ed07
Source dataset
Borylation dataset from Roche

Reaction notes

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