Abstract
A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, Intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.
| Original language | English |
|---|---|
| Pages (from-to) | 202-209 |
| Number of pages | 8 |
| Journal | Journal of the American Chemical Society |
| Volume | 128 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 11 2006 |
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ASJC Scopus subject areas
- Chemistry(all)
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Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation : Synthesis of phthalimidine and indene derivatives. / Kuninobu, Yoichiro; Tokunaga, Yukimi; Kawata, Atsushi; Takai, Kazuhiko.
In: Journal of the American Chemical Society, Vol. 128, No. 1, 11.01.2006, p. 202-209.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation
T2 - Synthesis of phthalimidine and indene derivatives
AU - Kuninobu, Yoichiro
AU - Tokunaga, Yukimi
AU - Kawata, Atsushi
AU - Takai, Kazuhiko
PY - 2006/1/11
Y1 - 2006/1/11
N2 - A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, Intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.
AB - A rhenium complex, [ReBr(CO)3(thf)]2, catalyzes the reaction of an aromatic aldimine with an isocyanate and an acetylene to give a phthalimidine and an indene derivative in a quantitative yield, respectively. The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, Intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination. In contrast to ruthenium and rhodium catalysts, which are usually employed in this type of reaction, the rhenium catalyst promotes the insertion of a polar unsaturated molecule. This occurs more easily than the insertion of a nonpolar unsaturated molecule.
UR - http://www.scopus.com/inward/record.url?scp=30844466406&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=30844466406&partnerID=8YFLogxK
U2 - 10.1021/ja054216i
DO - 10.1021/ja054216i
M3 - Article
C2 - 16390148
AN - SCOPUS:30844466406
VL - 128
SP - 202
EP - 209
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 1
ER -