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A new reduction system by the combination of lanthanoid metals (Ln) and Lnl 2 : Deoxygenative coupling of amides to vic ‐diaminoalkenes
Author(s) -
Ogawa Akiya,
Nanke Taizoh,
Takami Noriaki,
Sekiguchi Masahito,
Kambe Nobuaki,
Sonoda Noboru
Publication year - 1995
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590090514
Subject(s) - ytterbium , chemistry , metal , lanthanide , sulfur , combinatorial chemistry , coupling (piping) , organic chemistry , doping , optoelectronics , metallurgy , ion , physics , materials science
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 YbI 2 is used alone. These results suggest novel enhancement of reducing ability by the combination of ytterbium(0) and ytterbium(II) diiodide. The Yb/YbI 2 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/SmI 2 mixed system.