3-Methylbenzaldehyde → (3-Formyl-5-methylphenyl)boronic acid pinacol ester

HRID 1490627Notes

Reaction equation

HRID 1490627 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+].Cc1cnc2c(ccc3c(C)c(C)cnc32)c1C.[Ir].[Ir]>Cc1cc(C=O)cc(B2OC(C)(C)C(C)(C)O2)c1

Participants

8

Reactant 1

HCID 121053-Methylbenzaldehyde

Product 1

HCID 127263689(3-Formyl-5-methylphenyl)boronic acid pinacol esterYield 79%

Reagents, catalysts & solvents 6

HCID 6385Tert-ButylamineReagentHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineReagentHCID 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-02e529dadf584eb2ad65978440415c1a
Source dataset
Borylation dataset from Roche

Reaction notes

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