On-water chemistry:: Copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water

被引:145
作者
Carril, M [1 ]
SanMartin, R [1 ]
Tellitu, I [1 ]
Domínguez, E [1 ]
机构
[1] Euskal Herriko Unibertsitatea, Kimika Organikoa Saila 2, Zientzia Eta Teknol Fak, Bilbao 48080, Spain
关键词
D O I
10.1021/ol060274c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A more sustainable protocol leading to 2-alkyl- or 2-aryl-substituted benzo[b]furans is reported, involving a copper-TMEDA complex which catalyzes the transformation of readily available ketone derivatives into the corresponding benzofurans in good to excellent yields. The reaction is accomplished using water as the solvent without organic cosolvents, and one example of catalyst reutilization is also presented.
引用
收藏
页码:1467 / 1470
页数:4
相关论文
共 21 条
[1]   An advantageous route to oxcarbazepine (Trileptal) based on palladium-catalyzed arylations free of transmetallating agents [J].
Carril, M ;
SanMartin, R ;
Churruca, F ;
Tellitu, I ;
Domínguez, E .
ORGANIC LETTERS, 2005, 7 (22) :4787-4789
[2]   Synthesis of benzo[b]furans via CuI-catalyzed ring closure [J].
Chen, CY ;
Dormer, PG .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17) :6964-6967
[3]   A new, expeditious entry to the benzophenanthrofuran framework by a Pd-catalyzed C- and O-arylation/PIFA-mediated oxidative coupling sequence [J].
Churruca, F ;
SanMartin, R ;
Tellitu, I ;
Domínguez, E .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (12) :2481-2490
[4]  
Genet JP, 1999, J ORGANOMET CHEM, V576, P305
[5]   Formation of aryl-nitrogen bonds using a soluble copper(I) catalyst [J].
Gujadhur, R ;
Venkataraman, D ;
Kintigh, JT .
TETRAHEDRON LETTERS, 2001, 42 (29) :4791-4793
[6]   Total synthesis and determination of the absolute configuration of frondosin B [J].
Inoue, M ;
Carson, MW ;
Frontier, AJ ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (09) :1878-1889
[7]  
KAPLARS A, 2002, J AM CHEM SOC, V124, P7421
[8]   Novel syntheses of 2,3-disubstituted benzofurans [J].
Katritzky, AR ;
Ji, Y ;
Fang, Y ;
Prakash, I .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (16) :5613-5615
[9]   Halogen-metal exchange/cyclization of iodoketones: A direct synthesis of 3-arylbenzofurans [J].
Kraus, GA ;
Schroeder, JD .
SYNLETT, 2005, (16) :2504-2506
[10]   Synthetic approach to malibatol A [J].
Kraus, GA ;
Kim, L .
ORGANIC LETTERS, 2003, 5 (08) :1191-1192