A new reduction system by the combination of lanthanoid metals (Ln) and Lnl2: Deoxygenative coupling of amides to vic‐diaminoalkenes

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Abstract
Deoxygenative coupling of aromatic amides takes place successfully by the use of a mixed system comprising of ytterbium metal and ytterbium diiodide, providing the corresponding vic‐diaminoalkenes in good yields. The same reaction does not take place if Yb metal or YbI2 is used alone. These results suggest novel enhancement of reducing ability by the combination of ytterbium(0) and ytterbium(II) diiodide. The Yb/YbI2 system is also effective for dethiolative coupling of thioamides, as sulfur analogues of amides. This paper also deals with reductive coupling of thioamides and selenoamides by using an Sm/SmI2 mixed system.