1-Phenylisoquinoline → 1-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]isoquinoline

HRID 1491495

Reaction equation

HRID 1491495 reaction equation
c1ccc(-c2nccc3ccccc23)cc1>C(=NN(Cc1ccccc1)Cc1ccccc1)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(c2ccccc2-c2nccc3ccccc23)OC1(C)C

Participants

7

Reactant 1

HCID 1378821-Phenylisoquinoline

Product 1

HCID 1407864431-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]isoquinolineYield 78%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagentHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagentHCID 67601456N,N-Dibenzyl-N'-(pyridin-2-ylmethylene)hydrazineReagentHCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Following the general procedure, precipitation from the reaction crude with hexane, trituration and filtration afforded 9n (132 mg, 80 %) as a light brown solid.

Sources & evidence

ORD record
ord-9cd5a8a6d6f84ea8b68e2222fc75d190
Source dataset
Borylation dataset from Roche

Linked notes

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