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HRID 2217026作成日:2026年10月27日

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

https://huagongshe.com/reaction/2217026

反応式

関与物質

役割名称HCID仕込み量
反応物1,10-PhenanthrolineHCID 1318—
反応物IodobenzeneHCID 11575—
反応物2,9-Dimethyl-1,10-phenanthrolineHCID 65237—
反応物BenzeneselenolHCID 69530—
反応物Sodium t-butoxideHCID 23676156—
触媒CuI neocuproineHCID 86760266—
溶媒TolueneHCID 1140—
生成物Benzene, 1,1'-selenobis-HCID 14333—

反応手順

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).

情報源と証拠

DOI10.6084/m9.figshare.5104873.v1
特許番号US07112697B1
出典データセットuspto-grants-2006_09
ORD IDord-b6e56939b33641dfadc6d291d35e4c94
出典メモuspto-grants-2006_09