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

HRID 1491147Notes

Reaction equation

HRID 1491147 reaction equation
CSc1cccc(C)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)cc(B2OC(C)(C)C(C)(C)O2)c1.CSc1cc(C)ccc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 21005Benzene, 1-methyl-3-(methylthio)-

Product 2

HCID 1383758734,4,5,5-Tetramethyl-2-(4-methyl-2-(methylthio)phenyl)-1,3,2-dioxaborolaneYield 10%HCID 1648918854,4,5,5-Tetramethyl-2-(3-methyl-5-(methylthio)phenyl)-1,3,2-dioxaborolaneYield 52%

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 (82 mg, 62% yield, ortho/meta + para = 0.16); meta-Isomer 5j was obtained by further purification by GPC (65 mg, 48% yield), white solid;

Sources & evidence

ORD record
ord-5c6ce2a28c9749d281016644e487345d
Source dataset
Borylation dataset from Roche

Reaction notes

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