A Direct, Copper-Catalyzed Functionalization of Pyridines with Alkynes

被引:22
作者
Beveridge, Ramsay E. [1 ,2 ]
Arndtsen, Bruce A. [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[2] Pfizer Global Res & Dev, Groton, CT 06340 USA
来源
SYNTHESIS-STUTTGART | 2010年 / 06期
基金
加拿大自然科学与工程研究理事会;
关键词
pyridine; copper; catalytic; alkyne; alkene; CROSS-COUPLING REACTIONS; 1-ACYLPYRIDINIUM SALTS; N-OXIDES; STEREOSELECTIVE-SYNTHESIS; MULTICOMPONENT SYNTHESIS; REGIOSELECTIVE ADDITION; EFFICIENT SYNTHESIS; DIRECT ARYLATION; ACID-CHLORIDES; ONE-STEP;
D O I
10.1055/s-0029-1218632
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-pot, copper-catalyzed method to construct 2-alkynylpyridines is presented. This provides a route to access these products directly from terminal alkynes and the parent pyridine, and without prefunctionalization of the pyridine core. In addition, (Z)-alk-2-enylpyridines can be prepared via a related procedure. These reactions are used to synthesize a number of new alkynyl- and alkenyl-substituted pyridines in one pot.
引用
收藏
页码:1000 / 1008
页数:9
相关论文
共 91 条
[1]   REACTION OF SILVER ACETYLIDE WITH ACYLPYRIDINIUM SALTS - N-BENZOYL-2-PHENYLETHYNYL-1,2-DIHYDROPYRIDINE [J].
AGAWA, T ;
MILLER, SI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (02) :449-&
[2]   Synthesis and receptor assay of aromatic-ethynyl-aromatic derivatives with potent mGluR5 antagonist activity [J].
Alagille, D ;
Baldwin, RM ;
Roth, BL ;
Wroblewski, JT ;
Grajkowska, E ;
Tamagnan, GD .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (01) :197-209
[3]  
Albrecht M, 2001, ANGEW CHEM INT EDIT, V40, P3750, DOI 10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO
[4]  
2-6
[5]   Bispyridylamides - coordination chemistry and applications in catalytic reactions [J].
Belda, O ;
Moberg, C .
COORDINATION CHEMISTRY REVIEWS, 2005, 249 (5-6) :727-740
[6]   A Suzuki-Miyaura approach to a series of forensically relevant pyridines [J].
Blachut, Dariusz ;
Czarnocki, Zbigniew ;
Wojtasiewicz, Krystyna .
SYNTHESIS-STUTTGART, 2006, (17) :2855-2864
[7]   General approach to the coupling of organoindium reagents with imines via copper catalysis [J].
Black, DA ;
Arndtsen, BA .
ORGANIC LETTERS, 2006, 8 (10) :1991-1993
[8]   Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes:: A multicomponent synthesis of α-substituted amides [J].
Black, DA ;
Arndtsen, BA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5133-5138
[9]   Copper-catalyzed coupling of imines, acid chlorides, and alkynes: A multicomponent route to propargylamides [J].
Black, DA ;
Arndtsen, BA .
ORGANIC LETTERS, 2004, 6 (07) :1107-1110
[10]   Copper-catalyzed coupling of pyridines and quinolines with alkynes: A one-step, asymmetric route to functionalized heterocycles [J].
Black, Daniel A. ;
Beveridge, Ramsay E. ;
Arndtsen, Bruce A. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1906-1910