4-Chlorobenzaldehyde 2,2-dimethylhydrazone → HCID 178484938, compound

HRID 1491502Notes

Reaction equation

HRID 1491502 reaction equation
CN(C)N=Cc1ccc(Cl)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]>CN(C)N=Cc1ccc(Cl)cc1B1OC(C)(C)C(C)(C)O1

Participants

7

Reactant 1

HCID 2112214-Chlorobenzaldehyde 2,2-dimethylhydrazone

Product 1

HCID 178484938HCID 178484938, compoundYield 73%

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
80 °C

Procedure

Following the general procedure, column chromatography in neutral alumina (EtOAc/n-hexane 1:10) afforded 11g (112 mg, 73 %).

Sources & evidence

ORD record
ord-4f76430a1a884af5b1fb0714cab85713
Source dataset
Borylation dataset from Roche

Reaction notes

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