2'-Methoxyacetophenone → 1-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone

HRID 1490928Notes

Reaction equation

HRID 1490928 reaction equation
COc1ccccc1C(C)=O>C1=CCCC=CCC1.C1=CCCC=CCC1.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)ccn2)c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.COC(C)(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>COc1cc(B2OC(C)(C)C(C)(C)O2)ccc1C(C)=O.COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C(C)=O

Participants

7

Reactant 1

HCID 684812'-Methoxyacetophenone

Product 2

HCID 586298631-[2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanoneYield 89%HCID 129984304HCID 129984304, compoundYield 11%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
25 °C

Procedure

General procedure Cwas applied to 1-(2-methoxyphenyl)ethanone15d(60mg, 0.4mmol). The reaction mixture was stirredat room temperature for 16hours giving a conversion of >99% (GC-MS) and 16dand 17din a 89:11mixture(1H NMR spectrum)and some unreacted starting material 15d.

Sources & evidence

ORD record
ord-c42ab34778ba41929035b71d38ce5430
Source dataset
Borylation dataset from Roche

Reaction notes

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