Copper-Catalyzed C-O Bond Formation: An Efficient One-Pot Highly Regioselective Synthesis of Furans from (2-Furyl)Carbene Complexes

被引:126
作者
Cao, Hua [1 ]
Zhan, Haiying [1 ]
Cen, Jinghe [1 ]
Lin, Jingxin [1 ]
Lin, Yuanguang [1 ]
Zhu, Qiuxia [1 ]
Fu, Minling [1 ]
Jiang, Huanfeng [2 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China
[2] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
关键词
FISCHER CARBENE COMPLEXES; ELECTRON-DEFICIENT ALKYNES; 2,3-ALLENOIC ACIDS; DOMINO PROCESS; 2,5-DISUBSTITUTED FURANS; POLYSUBSTITUTED FURANS; BIOLOGICAL EVALUATION; CYCLIZATION REACTION; KETONES; DERIVATIVES;
D O I
10.1021/ol400080e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient one-pot Cu(I)-catalyzed strategy for regioselective synthesis of trisubstituted furan derivatives has been developed via (2-furyl) carbene complexes. This process has opened a new synthetic route to a variety of alpha-carbonyl furans using air as the oxidant affording furans in good yields.
引用
收藏
页码:1080 / 1083
页数:4
相关论文
共 55 条
[1]  
[Anonymous], 2009, ANGEW CHEM
[2]   Metal-controlled selective [3+2] cyclization reactions of alkenyl Fischer carbene complexes and allenes [J].
Barluenga, J ;
Vicente, R ;
Barrio, P ;
López, LA ;
Tomás, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5974-5975
[3]   [3+2] cycloaddition of Fischer alkenyl carbene complexes to enamines:: An efficient asymmetric approach to cyclopentanoids [J].
Barluenga, J ;
Tomás, M ;
Ballesteros, A ;
Santamaría, J ;
Brillet, C ;
García-Granda, S ;
Piñera-Nicolás, A ;
Vázquez, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4516-4517
[4]   Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes [J].
Barluenga, Jose ;
Riesgo, Lorena ;
Vicente, Ruben ;
Lopez, Luis A. ;
Tomas, Miguel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13528-+
[5]   A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3+2] cyclization of alkenyl Fischer carbene complexes and internal alkynes [J].
Barluenga, Jose ;
Barrio, Pablo ;
Riesgo, Lorena ;
Lopez, Luis. A. ;
Tomas, Miguel .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) :14422-14426
[6]   Enantioselective Carbonyl Allylation, Crotylation, and tert-Prenylation of Furan Methanols and Furfurals via Iridium-Catalyzed Transfer Hydrogenation [J].
Bechem, Benjamin ;
Patman, Ryan L. ;
Hashmi, A. Stephen K. ;
Krische, Michael J. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1795-1798
[7]   N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes [J].
Biju, Akkattu T. ;
Wurz, Nathalie E. ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :5970-+
[8]   Design, synthesis, and biological activity of prazosin-related antagonists.: Role of the piperazine and furan units of prazosin on the selectivity for α1-adrenoreceptor subtypes [J].
Bolognesi, ML ;
Budriesi, R ;
Chiarini, A ;
Poggesi, E ;
Leonardi, A ;
Melchiorre, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4844-4853
[9]  
Cao H., 2011, ORG BIOMOL CHEM, V21, P7257
[10]   Transition-Metal-Catalyzed Domino Reactions: Efficient One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans from Electron-Deficient Alkynes and 2-Yn-1-ols [J].
Cao, Hua ;
Jiang, Huanfeng ;
Huang, Huawen .
SYNTHESIS-STUTTGART, 2011, (07) :1019-1036