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 language | English |
|---|---|
| Pages (from-to) | 11368-11369 |
| Number of pages | 2 |
| Journal | Journal of the American Chemical Society |
| Volume | 128 |
| Issue number | 35 |
| DOIs | |
| Publication status | Published - Sep 6 2006 |
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ASJC Scopus subject areas
- Chemistry(all)
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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
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TY - JOUR
T1 - Efficient catalytic insertion of acetylenes into a carbon-carbon single bond of nonstrained cyclic compounds under mild conditions
AU - Kuninobu, Yoichiro
AU - Kawata, Atsushi
AU - Takai, Kazuhiko
PY - 2006/9/6
Y1 - 2006/9/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=33748356066&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=33748356066&partnerID=8YFLogxK
U2 - 10.1021/ja064022i
DO - 10.1021/ja064022i
M3 - Article
C2 - 16939256
AN - SCOPUS:33748356066
VL - 128
SP - 11368
EP - 11369
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 35
ER -