Tandem Cyclizations of 1,6-Enynes with Arylsulfonyl Chlorides by Using Visible-Light Photoredox Catalysis

被引:183
作者
Deng, Guo-Bo [1 ]
Wang, Zhi-Qiang [1 ,2 ]
Xia, Jia-Dong [1 ,2 ]
Qian, Peng-Cheng [1 ]
Song, Ren-Jie [1 ]
Hu, Ming [2 ]
Gong, Lu-Bin [1 ]
Li, Jin-Heng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Hunan, Peoples R China
[2] Hunan Normal Univ, Minist Educ, Key Lab Chem Biol & Tradit Chinese Med Res, Changsha 410081, Hunan, Peoples R China
关键词
arylsulfonyl chlorides; cyclizations; enynes; ruthenium; visible-light photocatalysis; C-H ARYLATION; PHOTOCHEMICAL C-2-C-6 CYCLIZATION; DIELS-ALDER CYCLOADDITIONS; ENYNE-ALLENES; PSCHORR REACTION; DIAZONIUM SALTS; PHOTOCATALYSIS; PHOTOOXIDATION; CYCLOISOMERIZATION; FUNCTIONALIZATION;
D O I
10.1002/anie.201208380
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Ray of light: 10a,11-Dihydro-10H-benzo[b]fluorenes were synthesized by a visible-light-catalyzed tandem cyclization of 1,6-enynes with arylsulfonyl chlorides. This method extends the scope of enyne cyclizations and represents a new synthetic application of arylsulfonyl chlorides. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1535 / 1538
页数:4
相关论文
共 92 条
[1]   C1-C5 photochemical cyclization of enediynes [J].
Alabugin, IV ;
Kovalenko, SV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (31) :9052-9053
[2]  
Allard S., 2008, Angew. Chem, V120, P4138
[3]   Organic semiconductors for solution-processable field-effect transistors (OFETs) [J].
Allard, Sybille ;
Forster, Michael ;
Souharce, Benjamin ;
Thiem, Heiko ;
Scherf, Ullrich .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (22) :4070-4098
[4]  
[Anonymous], ANGEW CHEM
[5]   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
[6]   THE INTRAMOLECULAR DIELS-ALDER REACTION [J].
BRIEGER, G ;
BENNETT, JN .
CHEMICAL REVIEWS, 1980, 80 (01) :63-97
[7]   Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].
Bruneau, C .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334
[8]   Photochemical C2-C6 Cyclization of Enyne-Allenes: Detection of a Fulvene Triplet Diradical in the Laser Flash Photolysis [J].
Bucher, Goetz ;
Mahajan, Atul A. ;
Schmittel, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (22) :8815-8828
[9]   The Photochemical C2-C6 Cyclization of Enyne-Allenes: Interception of the Fulvene Diradical with a Radical Clock Ring Opening [J].
Bucher, Goetz ;
Mahajan, Atul A. ;
Schmittel, Michael .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :5850-5860
[10]   PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES [J].
CANOYELO, H ;
DERONZIER, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1984, (06) :1093-1098