2-Methylacetophenone → 1-[2-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone

HRID 1490930Notes

Reaction equation

HRID 1490930 reaction equation
CC(=O)c1ccccc1C>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]>CC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1C.CC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1C

Participants

7

Reactant 1

HCID 113402-Methylacetophenone

Product 2

HCID 754871961-[2-methyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanoneYield 49%HCID 1299466461-[2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanoneYield 38%

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’-methylphenyl)ethanone15f(54mg, 0.4mmol). The reaction mixture was was stirredat room temperature for 16hours giving a conversion of 87%(GC-MS) and 16fand 17fin a 56:44 mixture which also contained unreacted starting material 15f(1H NMRspectrum).

Sources & evidence

ORD record
ord-7774858fb93f41f7b91cc112210ae5ae
Source dataset
Borylation dataset from Roche

Reaction notes

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