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2001
C-C bond formation
C-C bond formation
O 0282
Generation and Reactions of Alkynylsamariums. — Alkynylsamarium
16 - 074 reagents can be generated on three different ways: (a) by reduction of alkynyl
iodides (I) with SmI2 in the presence of HMPA, (b) by deprotonation of
terminal alkynes (XI) with in situ formed tetrahydrofuranylsamarium, and (c)
by metal–metal exchange of alkynyllithium reagents with SmI3 . The generated
alkynylsamarium reagents can undergo Barbier or Grignard type reactions
with various electrophiles, e.g. carbonyl compounds, alkyl halides, or acid
anhydrides. The reaction mechanism is studied in detail using model reactions.
Interestingly, for the second method to generate alkynylsamarium reagents from
terminal alkynes, the use of alkylsamariums other than tetrahydrofuranylsamarium is unsuccessful. — (KUNISHIMA, MUNETAKA; NAKATA, DAISUKE;
TANAKA, SHINOBU; HIOKI, KAZUHITO; TANI, SHOHEI; Tetrahedron
56 (2000) 51, 9927-9935; Fac. Pharm. Sci., Kobe Gakuin Univ., Nishi, Kobe
651-21, Japan; EN)
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