3-Chlorophenyl methyl sulfide → HCID 138982779, compound

HRID 1491154Notes

Reaction equation

HRID 1491154 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.FC(F)(F)C1COB(c2ccccc2-c2ccc(-c3ccccn3)nc2)O1.[Ir].[Ir]>CSc1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.CSc1cc(Cl)ccc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 975853-Chlorophenyl methyl sulfide

Product 2

HCID 532172452-[3-Chloro-5-(methylsulfanyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 10%HCID 138982779HCID 138982779, compoundYield 54%

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 (91 mg, 64% yield, ortho/meta + para = 5.1); ortho-borylated product 4n was obtained by further purification by GPC (60 mg, 42% yield), colorless oil;

Sources & evidence

ORD record
ord-6861f89fef964ee69d79922c8ba7d19d
Source dataset
Borylation dataset from Roche

Reaction notes

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