3-Methylbenzaldehyde → 5-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

HRID 1490621Notes

Reaction equation

HRID 1490621 reaction equation
Cc1cccc(C=O)c1>C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC(C)(C)N.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].Nc1cccc2cccnc12.[Ir].[Ir]>Cc1ccc(B2OC(C)(C)C(C)(C)O2)c(C=O)c1

Participants

8

Reactant 1

HCID 121053-Methylbenzaldehyde

Product 1

HCID 581396965-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeYield 81%

Reagents, catalysts & solvents 6

HCID 6385Tert-ButylamineReagentHCID 113598-AminoquinolineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Sources & evidence

ORD record
ord-95af14ff1a5441ce81be1c87383fb742
Source dataset
Borylation dataset from Roche

Reaction notes

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