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

HRID 1491144Notes

Reaction equation

HRID 1491144 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.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>COc1ccc(B2OC(C)(C)C(C)(C)O2)c(SC)c1

Participants

6

Reactant 1

HCID 2811823-Methoxythioanisole

Product 1

HCID 1389831022-(4-Methoxy-2-(methylthio)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 60%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 1349566232-Pyridin-2-yl-5-[2-[4-(trifluoromethyl)-1,3,2-dioxaborolan-2-yl]phenyl]pyridineReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
55 °C

Procedure

Ligand 3f: A mixture of ortho- and meta-borylated products (84 mg, 60% yield, ortho/meta + para = >30); ortho-borylated product 4i was obtained by further purification by GPC (71 mg, 51% yield), colorless oil;

Sources & evidence

ORD record
ord-7487af86acf14633b8eaaa84b7fb2b65
Source dataset
Borylation dataset from Roche

Reaction notes

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