Reactions between tantalum- or niobium-alkyne complexes and carbonyl compounds

Yasutaka Kataoka, Jiro Miyai, Koichiro Oshima, Kazuhiko Takai, Kiitiro Utimoto

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

A variety of tantalum-alkyne complexes are generated in situ by treatment of alkynes with low-valent tantalum derived from TaCl5 and zinc. These complexes add regioselectively to carbonyl compounds in a one-to-one fashion to yield (E)-allylic alcohols stereoselectively. Iodinolysis of the oxatantalacyclopentene, which is postulated as an intermediate of the reaction, gives a (Z)-3-iodo-2-propen-1-ol derivative. In contrast to tantalum-alkyne complexes, niobium-alkyne complexes, prepared with low-valent niobium derived from NbCl5 and zinc, add in situ to aldehydes in a one-to-two fashion to give 1,3-diene derivatives. The dienes are produced through (i) addition of the alkyne complexes with 2 equiv of aldehydes at cis vicinal positions of the alkenes and (ii) deoxygenative elimination of 2,7-dioxanioba-4-cycloheptene complexes.

Original languageEnglish
Pages (from-to)1973-1981
Number of pages9
JournalJournal of Organic Chemistry
Volume57
Issue number7
Publication statusPublished - 1992
Externally publishedYes

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Niobium
Tantalum
Carbonyl compounds
Alkynes
Aldehydes
Zinc
Derivatives
Alkenes

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kataoka, Y., Miyai, J., Oshima, K., Takai, K., & Utimoto, K. (1992). Reactions between tantalum- or niobium-alkyne complexes and carbonyl compounds. Journal of Organic Chemistry, 57(7), 1973-1981.

Reactions between tantalum- or niobium-alkyne complexes and carbonyl compounds. / Kataoka, Yasutaka; Miyai, Jiro; Oshima, Koichiro; Takai, Kazuhiko; Utimoto, Kiitiro.

In: Journal of Organic Chemistry, Vol. 57, No. 7, 1992, p. 1973-1981.

Research output: Contribution to journalArticle

Kataoka, Y, Miyai, J, Oshima, K, Takai, K & Utimoto, K 1992, 'Reactions between tantalum- or niobium-alkyne complexes and carbonyl compounds', Journal of Organic Chemistry, vol. 57, no. 7, pp. 1973-1981.
Kataoka, Yasutaka ; Miyai, Jiro ; Oshima, Koichiro ; Takai, Kazuhiko ; Utimoto, Kiitiro. / Reactions between tantalum- or niobium-alkyne complexes and carbonyl compounds. In: Journal of Organic Chemistry. 1992 ; Vol. 57, No. 7. pp. 1973-1981.
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