1,10-Phenanthroline → Benzene, 1,1'-selenobis-

HRID 2217026

Reaction equation

HRID 2217026 reaction equation
[C:1]1([SeH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[Na+].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.C1(C)C=CC=CC=1>[C:1]1([Se:7][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 13181,10-PhenanthrolineHCID 11575IodobenzeneHCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 69530Benzeneselenol2×HCID 23676156Sodium t-butoxide

Product 1

HCID 14333Benzene, 1,1'-selenobis-

Reagents, catalysts & solvents 2

HCID 86760266CuI neocuproineCatalystHCID 1140TolueneSolvent

Procedure

In a similar manner, the cross-coupling reaction between aryl iodides and phenyl selenol was initially investigated using 10 mol % CuI/neocuproine with NaOt-Bu as the base and toluene as the solvent. Using this protocol, in 24 h, the reaction between iodobenzene and phenyl selenol was complete. If in the reaction protocol neocuproine was replaced by phenanthroline, diphenyl selenide was obtained in a lower yield (70% by GC). Moreover, the reaction with the well-defined complex Cu-(neocuproine)(PPh3)Br showed complete conversion to the product after the same period of time. Use of CuI/neocuproine as catalyst, instead of the well-defined Cu(neocuproine)(PPh3)Br, dispenses with the need to synthesize the complex and the results are comparable. The effect of the base on such reactions (see Table 4).

Sources & evidence

ORD record
ord-b6e56939b33641dfadc6d291d35e4c94
Source dataset
uspto-grants-2006_09
Patent number
US07112697B1

Linked notes

Loading…