Oxidative Homocoupling of Diheteroaryl- or Diarylmanganese Reagents Generated via Directed Manganation Using TMP2Mn

被引:11
作者
Haas, Diana [1 ]
Hammann, Jeffrey M. [1 ]
Moyeux, Alban [2 ,3 ]
Cahiez, Gerard [2 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] CNRS Chim ParisTech, Inst Rech Chim Paris, F-75005 Paris, France
[3] Univ Paris 13, Sorbonne Paris Cite, F-93017 Bobigny, France
关键词
homocoupling; manganese; metalation; dimerization; oxidation; CROSS-COUPLING REACTIONS; CENTER-DOT-LICL; CHEMOSELECTIVE MULTIPLE FUNCTIONALIZATION; ORTHO-METALATION; IONIC LIQUIDS; ORGANIC-SYNTHESIS; BOND FORMATION; ARYL HALIDES; DERIVATIVES; NICKEL;
D O I
10.1055/s-0034-1380424
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report an oxidative homocoupling of diheteroaryl or diarylmanganese reagents prepared by directed manganation using TMP(2)Mn2MgCl(2)4LiCl. The resulting diorganomanganese reagents can efficiently undergo an oxidative dimerization leading to the homocoupling products in good yields. Remarkably, a number of functional groups, as well as sensitive heterocycles are tolerated using this metalation-dimerization procedure.
引用
收藏
页码:1515 / 1519
页数:5
相关论文
共 62 条
[1]   Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives:: A one-pot protocol to substituted azabiaryls [J].
Alessi, Manlio ;
Larkin, Andrew L. ;
Ogilvie, Kevin A. ;
Green, Laine A. ;
Lai, Sunny ;
Lopez, Simon ;
Snieckus, Victor .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) :1588-1594
[2]   Synthesis of conjugatively bridged bis- and tris-5-(2,2′-bipyridines):: Multitopic metal ion-binding modules for supramolecular nanoengineering [J].
Baxter, PNW .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (05) :1257-1272
[3]   Aryl-aryl bonds formation in pyridine and diazine series.: Diazines part 41 [J].
Boully, L ;
Darabantu, M ;
Turck, A ;
Plé, N .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (07) :1423-1428
[4]   Selective Magnesiation or Zincation of Highly Functionalized Alkenes and Cycloalkenes Using 2,2,6,6-Tetramethylpiperidyl Bases [J].
Bresser, Tomke ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (08) :1914-1917
[5]   Scaleable Preparation of Sensitive Functionalized Aromatics and Heteroaromatics via Directed Metalation Using tmpZnCl•LiCl [J].
Bresser, Tomke ;
Monzon, Gabriel ;
Mosrin, Marc ;
Knochel, Paul .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (06) :1299-1303
[6]   Regio- and Chemoselective Zincation of Sensitive and Moderately Activated Aromatics and Heteroaromatics Using TMPZnCl•LiCl [J].
Bresser, Tomke ;
Mosrin, Marc ;
Monzon, Gabriel ;
Knochel, Paul .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (14) :4686-4695
[7]   Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents [J].
Cahiez, G ;
Chaboche, C ;
Mahuteau-Betzer, F ;
Ahr, M .
ORGANIC LETTERS, 2005, 7 (10) :1943-1946
[8]   Manganese- or iron-catalyzed homocoupling of Grignard reagents using atmospheric oxygen as an oxidant [J].
Cahiez, Gerard ;
Moyeux, Alban ;
Buendia, Julien ;
Duplais, Christophe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) :13788-+
[9]   Recent developments in catalytic aryl coupling reactions [J].
Catellani, Marta ;
Motti, Elena ;
Della Ca, Nicola ;
Ferraccioli, Raffaella .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (25) :4153-4165
[10]   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