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Lanthanoid‐Metal‐Mediated organic reactions of acyltrialkylsilanes
Author(s) -
Taniguchi Yuki,
Fujii Nobuto,
Takaki Ken,
Fujiwara Yuzo
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.590090504
Subject(s) - chemistry , lanthanide , silylation , nucleophile , electrophile , ytterbium , alcohol , iodide , samarium , metal , yield (engineering) , acetylene , organic chemistry , reagent , medicinal chemistry , catalysis , ion , physics , materials science , optoelectronics , doping , metallurgy
Abstract Aromatic acylsilanes such as benzoyltrimethylsilane react with ytterbium (Yb) metal to give the corresponding Yb‐oxametallacycle of the aromatic acylsilane. The Yb‐oxametallacycle thereby formed reacts with another aroylsilane to afford the symmetrical 1,2‐diarylacetylene in good yield. These nucleophilic Yb‐oxametallacycles have been found to react with a variety of electrophiles affording α‐silyl alcohol derivatives. In contrast, aliphatic acylsilanes are reduced with lanthanoid reagents such as Yb metal and samarium(II) iodide (SmI 2 ) to give α‐silyl alcohols, and the corresponding aliphatic acetylene was not obtained.