3-Methoxythioanisole → 2-(3-Methoxy-5-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 1491145Notes

Reaction equation

HRID 1491145 reaction equation
COc1cccc(SC)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]>COc1cc(SC)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

6

Reactant 1

HCID 2811823-Methoxythioanisole

Product 1

HCID 532172462-(3-Methoxy-5-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 69%

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 (97 mg, 69% yield, ortho/meta + para = <0.01); meta-Isomer 5i were obtained by further purification by GPC (92 mg, 66% yield), white solid (mp. 73-75 oC)

Sources & evidence

ORD record
ord-bc30bcc9f8fa4078b52bc21fad6778ea
Source dataset
Borylation dataset from Roche

Reaction notes

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