Isoquinoline, 1-(1-naphthalenyl)- → 1-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl]isoquinoline

HRID 1491485Notes

Reaction equation

HRID 1491485 reaction equation
c1ccc2c(-c3nccc4ccccc34)cccc2c1>C(=Nc1ccccc1)c1ccccn1.C1=CCCC=CCC1.C1=CCCC=CCC1.C1CCOC1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C.CC1(C)OBOC1(C)C.C[OH2+].C[OH2+].[Ir].[Ir]>CC1(C)OB(c2ccc3ccccc3c2-c2nccc3ccccc23)OC1(C)C

Participants

7

Reactant 1

HCID 3838254Isoquinoline, 1-(1-naphthalenyl)-

Product 1

HCID 1015479341-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl]isoquinolineYield 50%

Reagents, catalysts & solvents 5

HCID 499408trans-N-(2-Pyridylmethylene)anilineReagentHCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

Following the general procedure, column chromatography (EtOAc/nhexane 1:3) afforded 9a (160 mg, 84 %) as a light yellow solid. Evaporation from EtOAc/n-hexane afforded X-Ray quality crystals.

Sources & evidence

ORD record
ord-ae43fe88113a465f8385191940458550
Source dataset
Borylation dataset from Roche

Reaction notes

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