2-Methyl-2,3-dihydro-1H-isoindol-1-one → 2-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one

HRID 1490848Notes

Reaction equation

HRID 1490848 reaction equation
CN1Cc2ccccc2C1=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.C[OH2+].C[OH2+].Cc1ccc(C)cc1.[Ir].[Ir]>CN1Cc2cc(B3OC(C)(C)C(C)(C)O3)ccc2C1=O.CN1Cc2ccc(B3OC(C)(C)C(C)(C)O3)cc2C1=O

Participants

7

Reactant 1

HCID 2206572-Methyl-2,3-dihydro-1H-isoindol-1-one

Product 2

HCID 468564162-Methyl-6-(4,4,5,5-tetraMethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-oneYield 28%HCID 576912242-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneYield 26%

Reagents, catalysts & solvents 4

HCID 2733548Bis(pinacolato)diboraneReagentHCID 42491874,4'-Di-tert-butyl-2,2'-bipyridylReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
35 °C

Sources & evidence

ORD record
ord-4d9439b94bfa4113b4442f24c09c900d
Source dataset
Borylation dataset from Roche

Reaction notes

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