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

HRID 2217026

反応式

HRID 2217026 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 14333Benzene, 1,1'-selenobis-

試薬・触媒・溶媒 2

HCID 86760266CuI neocuproine触媒HCID 1140Toluene溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-b6e56939b33641dfadc6d291d35e4c94
出典データセット
uspto-grants-2006_09
特許番号
US07112697B1

関連ノート

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