Rhodium-Catalyzed Complete Regioselective Intermolecular Cross-Cyclotrimerization of Aryl Ethynyl Ethers and Nitriles or Isocyanates at Room Temperature

被引：81

作者：

Komine, Yoshiyuki ^{[1
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 06期

关键词：

2+2+2 CYCLOADDITION; ALKYNES; PYRIDINES; CONSTRUCTION; ACETYLENE;

D O I：

10.1021/ol100182u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have established that a cationic rhodium(I)/H-8-BINAP complex catalyzes the complete regloselective intermolecular cross-cyclotrimerization of aryl ethynyl ethers and nitriles or isocyanates leading to 2,4-diaryloxypyridines or 4,6-diaryloxy-2-pyridones at room temperature.

引用

页码：1312 / 1315

页数：4

共 23 条

[1] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes
Chopade, Pramod R.
Louie, Janis
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) : 2307 - 2327
[2] Beyond Reppe: Building Substituted Arenes by [2+2+2] Cycloadditions of Alkynes
Galan, Brandon R.
Rovis, Tomislav
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (16) : 2830 - 2834
[3] Photocatalyzed [2+2+2]-cycloaddition of nitriles with acetylene: An effective method for the synthesis of 2-pyridines under mild conditions
Heller, B
Sundermann, B
Buschmann, H
Drexler, HJ
You, JS
Holzgrabe, U
Heller, E
Oehme, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) : 4414 - 4422
[4] The fascinating construction of pyridine ring systems by transition metal-catalysed [2+2+2] cycloaddition reactions
Heller, Barbara
Hapke, Marko
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1085 - 1094
[5] Flexible Synthesis of Fused Benzofuran Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition with Phenol-Linked 1,6-Diynes
Komine, Yoshiyuki
Kamisawa, Akiyoshi
Tanaka, Ken
[J]. ORGANIC LETTERS, 2009, 11 (11) : 2361 - 2364
[6] Transition-metal-catalyzed reactions in heterocyclic synthesis
Nakamura, I
Yamamoto, Y
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2127 - 2198
[7] Regioselective rhodium-catalyzed intermolecular [2+2+2] cycloaddition of alkynes and isocyanates to form pyridones
Oberg, Kevin M.
Lee, Ernest E.
Rovis, Tornislav
[J]. TETRAHEDRON, 2009, 65 (26) : 5056 - 5061
[8] REACTION OF (AMINOCARBENE)IRON COMPLEXES WITH ALKYNES - A SYNTHESIS OF 5-AMINOFURANS
SEMMELHACK, MF
PARK, J
[J]. ORGANOMETALLICS, 1986, 5 (12) : 2550 - 2552
[9] Facile preparation of various heteroaromatic compounds via azatitanacyclopentadiene intermediates
Suzuki, D
Nobe, Y
Watai, Y
Tanaka, R
Takayama, Y
Sato, F
Urabe, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) : 7474 - 7479
[10] Metalative Reppe reaction. Organized assembly of acetylene molecules on titanium template leading to a new style of acetylene cyclotrimerization
Suzuki, D
Urabe, H
Sato, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (32) : 7925 - 7926

← 1 2 3 →