4-Phenylthioanisole → 4,4,5,5-Tetramethyl-2-(2-methylsulfanyl-5-phenylphenyl)-1,3,2-dioxaborolane

HRID 1491140

Reaction equation

HRID 1491140 reaction equation
CSc1ccc(-c2ccccc2)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.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>CSc1ccc(-c2ccccc2)cc1B1OC(C)(C)C(C)(C)O1

Participants

6

Reactant 1

HCID 110198974-Phenylthioanisole

Product 1

HCID 1325102624,4,5,5-Tetramethyl-2-(2-methylsulfanyl-5-phenylphenyl)-1,3,2-dioxaborolaneYield 86%

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 (140 mg, 86% yield, ortho/meta + para = >30); ortho-borylated product 4g was obtained by further purification by GPC (128 mg, 79% yield), white solid (mp. 116-118 oC)

Sources & evidence

ORD record
ord-a2d89378380b4f06b6a03649928343ec
Source dataset
Borylation dataset from Roche

Linked notes

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