Copper(I)-mediated oxidative cross-coupling between functionalized alkynyl lithium and aryl magnesium reagents

被引:71
作者
Dubbaka, Srinivas Reddy [1 ]
Kienle, Marcel [1 ]
Mayr, Herbert [1 ]
Knochel, Paul [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
关键词
alkynes; cross-coupling; cuprates; nitrogen heterocycles;
D O I
10.1002/anie.200703097
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) All crossed: The reaction of unsaturated copper reagents with various alkynyl lithium compounds provides mixed lithium cuprates, which in the presence of chloranil undergo an oxidative coupling, thus leading to polyfunctional alkynes or enynes. Bromoenynes prepared by this method are readily converted into pyridine derivatives by a new ring closure that proceeds at low temperature (see scheme, tol = tolyl). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:9093 / 9096
页数:4
相关论文
共 75 条
[1]   Palladium-assisted routes to nucleosides [J].
Agrofoglio, LA ;
Gillaizeau, I ;
Saito, Y .
CHEMICAL REVIEWS, 2003, 103 (05) :1875-1916
[2]   Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives [J].
Anastasia, L ;
Negishi, E .
ORGANIC LETTERS, 2001, 3 (20) :3111-3113
[3]  
[Anonymous], 2002, J ORGANOMET CHEM
[4]   First Sonogashira coupling reactions with the chlorobenzeneCr-(CO)2PPh3 complex [J].
Ansorge, M ;
Müller, TJJ .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 585 (01) :174-178
[5]   Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines [J].
Asao, N ;
Yudha, S ;
Nogami, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5526-5528
[6]  
Asao N., 2005, ANGEW CHEM, V117, P5662
[7]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[8]   Intermolecular oxidative enolate heterocoupling [J].
Baran, Phil S. ;
DeMartino, Michael P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (42) :7083-7086
[9]  
Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO
[10]  
2-X