Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions

Yoichiro Kuninobu, Atsushi Kawata, Kazuhiko Takai

Research output: Contribution to journal › Article

74 Citations (Scopus)

Abstract

A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of a 1,3-dicarbonyl cyclic compound with an acetylene to give a medium-sized cyclic compound in excellent yield. By using isocyanide as an additive, the catalytic activity of the rhenium complex changes dramatically, and the insertion of acetylenes into a carbon-carbon single bond occurs under mild conditions. A plausible mechanism is that the reaction proceeds via the formation of a rhenacyclopentene intermediate, ring opening by a retro-aldol reaction, isomerization, and reductive elimination.

Original languageEnglish
Pages (from-to)11368-11369
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number35
DOIs
Publication statusPublished - Sep 6 2006

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Rhenium
Alkynes
Acetylene
Carbon
Cyanides
Carbon Monoxide
Isomerization
Catalyst activity
single bond
3-hydroxybutanal

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions. / Kuninobu, Yoichiro; Kawata, Atsushi; Takai, Kazuhiko.

In: Journal of the American Chemical Society, Vol. 128, No. 35, 06.09.2006, p. 11368-11369.

Research output: Contribution to journal › Article

Kuninobu, Y, Kawata, A & Takai, K 2006, 'Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions', Journal of the American Chemical Society, vol. 128, no. 35, pp. 11368-11369. https://doi.org/10.1021/ja064022i
Kuninobu Y, Kawata A, Takai K. Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions. Journal of the American Chemical Society. 2006 Sep 6;128(35):11368-11369. https://doi.org/10.1021/ja064022i
Kuninobu, Yoichiro ; Kawata, Atsushi ; Takai, Kazuhiko. / Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 35. pp. 11368-11369.
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