Nitrative Cyclization of 1-Ethynyl-2-(vinyloxy)benzenes to Access 1-[2-(Nitromethyl)benzofuran-3-yl] Ketones Through Dioxygen Activation

被引:67
作者
Hu, Ming [1 ]
Liu, Bang [1 ]
Ouyang, Xuan-Hui [1 ]
Song, Ren-Jie [1 ]
Li, Jin-Heng [1 ,2 ]
机构
[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
cyclization; dioxygen activation; enynes; nitration; CATALYZED CASCADE CYCLIZATION; FREE NITRO-CARBOCYCLIZATION; TERT-BUTYL NITRITE; CARBON TRIPLE BOND; C-C; RADICAL-ADDITION; ELECTROPHILIC ACTIVATION; AEROBIC OXYGENATION; MOLECULAR-OXYGEN; TERMINAL ALKYNES;
D O I
10.1002/adsc.201500336
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new metal-free method for the nitrative cyclization of 1-ethynyl-2-(vinyloxy) benzenes with tert-butyl nitrite (t-BuONO), air and water at room temperature is presented, in which an oxygen atom is introduced into the carbon-carbon triple bond to form a new carbonyl group through dioxygen activation.
引用
收藏
页码:3332 / 3340
页数:9
相关论文
共 118 条
[1]   Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[2]  
[Anonymous], FURANS SYNTHESIS APP
[3]  
[Anonymous], 2013, ANGEW CHEM
[4]  
[Anonymous], 2014, Angew. Chem
[5]  
[Anonymous], 1995, PALLADIUM REAGENTS C, DOI DOI 10.1021/ol101619s
[6]  
[Anonymous], 2014, ANGEW CHEM INT EDIT
[7]   Intermolecular oxidative cross-coupling of arenes [J].
Ashenhurst, James A. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :540-548
[8]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[9]  
Barton D., 1993, The Activation of Dioxygen and Homogeneous Catalytic Oxidation
[10]   Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].
Bruneau, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334