2-Methylanisole → HCID 69938122, compound

HRID 1490926Notes

Reaction equation

HRID 1490926 reaction equation
COc1ccccc1C>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.COc1ccc(B2OC(C)(C)C(C)(C)O2)cc1C

Participants

7

Reactant 1

HCID 336372-Methylanisole

Product 2

HCID 21923912HCID 21923912, compoundYield 19%HCID 69938122HCID 69938122, compoundYield 56%

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-methoxy-2-methylbenzene 15b(50mg, 0.4mmol). The reaction mixture was stirredat room temperature for 16hours giving a conversion of 75% (GC-MS) and 16band 17bin a 75:25mixture which also contained unreacted starting material 15b(1H NMR spectrum).

Sources & evidence

ORD record
ord-d706495cb5eb4f489882e939c637fd65
Source dataset
Borylation dataset from Roche

Reaction notes

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