1-Chloro-3-(methylthio)benzene → 2-(3-Chloro-5-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reaction equation

CSc1cccc(Cl)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(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

Conditions

Temperature: 55 °C

Procedure

dtbpy: A mixture of ortho- and meta-borylated products (107 mg, 75% yield, ortho/meta + para = <0.01); meta-iIsomer 5n was obtained by further purification by GPC (93 mg, 66% yield), yellow oil;

Sources & evidence

ORD record: ord-ea22c733887e472dac3d22ee72ddf6f5
Source dataset: Borylation dataset from Roche
DOI: 10.1002/anie.201610041

Reaction notes

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Participants

Reactant 1

HCID 975851-Chloro-3-(methylthio)benzene

Product 1

HCID 532172452-(3-Chloro-5-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 75%

Reagents, catalysts & solvents 4

HCID 143384,4'-Dimethyl-2,2'-bipyridineReagent

HCID 2733548Bis(pinacolato)diboraneReagent

HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalyst

HCID 7809P-XyleneSolvent