2,3-Functionalization of furans, benzofurans and thiophenes via magnesiation and sulfoxide-magnesium exchange

被引:58
作者
Melzig, Laurin [1 ]
Rauhut, Christian B. [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Munich, Germany
关键词
ALKENYL HALIDES; ROUTE; DERIVATIVES; REAGENTS; ARENES; ARYL;
D O I
10.1039/b907330b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The use of TMPMgCl center dot LiCl and iPrMgCl center dot LiCl allows a sequential 2,3-difunctionalization of various 2-arylsulfinyl furans, thiophenes and benzofurans. Subsequent use of the same reagents permits a selective full functionalization of all 4 positions of the furan and thiophene scaffolds.
引用
收藏
页码:3536 / 3538
页数:3
相关论文
共 22 条
[1]   Zinc Homologation-Elimination Reaction of α-Sulfinyl Carbanions as a New Route to Olefins [J].
Abramovitch, Adi ;
Marek, Ilan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (29) :4924-4931
[2]   HIGH-YIELD SYNTHESES OF DILITHIO-DERIVATIVES OF FURAN, THIOPHENE, N-METHYLPYRROLE, 3-METHYLFURAN, AND 3-METHYLTHIOPHEN - APPLICATION OF METHOD TO 2-METHYLFURAN, 2-METHYLTHIOPHEN, 2,5-DIMETHYLFURAN, 2,5-DIMETHYLTHIOPHEN, BENZO[B]FURAN, BENZO[B]THIOPHEN, PYRROLE, AND INDOLE [J].
CHADWICK, DJ ;
WILLBE, C .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :887-893
[3]   Direct magnesiation of polyfunctionalized arenes and heteroarenes using (tmp)2Mg-2LiCl [J].
Clososki, Giuliano C. ;
Rohbogner, Christoph J. ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (40) :7681-7684
[4]   REGIOSPECIFIC SYNTHESIS OF DISUBSTITUTED BENZENE-DERIVATIVES [J].
FELIX, G ;
DUNOGUES, J ;
CALAS, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (05) :402-404
[5]  
Fujiki K, 2002, SYNTHESIS-STUTTGART, P343
[6]  
Hou XL, 2003, PROG HET CH, V15, P167
[7]  
Keay B.A., 1997, Comprehensive Heterocyclic Chemistry II, V2, P395, DOI DOI 10.1016/B978-008096518-5.00047-2
[8]   A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides [J].
Krasovskiy, A ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3333-3336
[9]   Mixed Mg/Li amides of the type R2NMgCl•LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds [J].
Krasovskiy, Arkady ;
Krasovskaya, Valeria ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) :2958-2961
[10]   Use of furans in synthesis of bioactive compounds [J].
Lee, HK ;
Chan, KF ;
Hui, CW ;
Yim, HK ;
Wu, XW ;
Wong, HNC .
PURE AND APPLIED CHEMISTRY, 2005, 77 (01) :139-143