1,1-Dimethyl-2-[(naphthalen-1-yl)methylidene]hydrazine → HCID 178484931, compound

Reaction equation

CN(C)N=Cc1cccc2ccccc12>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=Cc1c(B2OC(C)(C)C(C)(C)O2)ccc2ccccc12

Participants

Conditions

Temperature: 80 °C

Procedure

Following the general procedure, column chromatography in neutral alumina (EtOAc/n-hexane 1:8) afforded 11i (155 mg, 95 %) as a yellow oil.

Sources & evidence

ORD record: ord-04ef4005b699487e9a1d97d3cb0cd4bf
Source dataset: Borylation dataset from Roche
DOI: 10.1002/anie.201104544

Reaction notes

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Participants

Reactant 1

HCID 3005081,1-Dimethyl-2-[(naphthalen-1-yl)methylidene]hydrazine

Product 1

HCID 178484931HCID 178484931, compoundYield 95%

Reagents, catalysts & solvents 5

HCID 2733548Bis(pinacolato)diboraneReagent

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneReagent

HCID 67601456N,N-Dibenzyl-N'-(pyridin-2-ylmethylene)hydrazineReagent

HCID 76001521Bis(1,5-cyclooctadiene)dimethoxydiiridiumCatalyst

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature: 80 °C

Procedure

Following the general procedure, column chromatography in neutral alumina (EtOAc/n-hexane 1:8) afforded 11i (155 mg, 95 %) as a yellow oil.

Sources & evidence

ORD record: ord-04ef4005b699487e9a1d97d3cb0cd4bf
Source dataset: Borylation dataset from Roche
DOI: 10.1002/anie.201104544

Reaction notes

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