Pd-Catalyzed Decarboxylative Coupling of Propiolic Adds: One-Pot Synthesis of 1,4-Disubstituted 1,3-Diynes via Sonogashira-Homocoupling Sequence

被引:82
作者
Park, Jihye [1 ]
Park, Eonjeong [1 ]
Kim, Aejin [1 ]
Park, Seul-A [1 ]
Lee, Youngil [1 ]
Chi, Ki-Whan [1 ]
Jung, Young Hoon [2 ]
Kim, In Su [1 ]
机构
[1] Univ Ulsan, Dept Chem, Ulsan 680749, South Korea
[2] Sungkyunkwan Univ, Sch Pharm, Suwon 440746, South Korea
基金
新加坡国家研究基金会;
关键词
ALKYNYL CARBOXYLIC-ACIDS; POTASSIUM POLYFLUOROBENZOATES; CONJUGATED OLIGOMERS; DIRECT ARYLATION; BENZOIC-ACIDS; ARYL; PANAXYTRIOL; HALIDES; KETONES;
D O I
10.1021/jo200096x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
One-pot synthesis of symmetric 1,4-disubstituted 1,3-diynes from iodoarenes and propiolic acid via Sonogashira reaction followed by Pd-catalyzed decarboxylative homocouplirtg is developed in high yields. Also, this system allows the one-pot synthesis of unsymmetric 1,4-disubstituted 1,3-diynes by cross-coupling of two different 3-substituted propiolic acids.
引用
收藏
页码:2214 / 2219
页数:6
相关论文
共 54 条
[1]  
Aida T, 2001, ANGEW CHEM INT EDIT, V40, P3803, DOI 10.1002/1521-3773(20011015)40:20<3803::AID-ANIE3803>3.0.CO
[2]  
2-T
[3]   3,4-Propylenedioxypyrrole-Based Conjugated Oligomers via Pd-Mediated Decarboxylative Cross Coupling [J].
Arroyave, Frank A. ;
Reynolds, John R. .
ORGANIC LETTERS, 2010, 12 (06) :1328-1331
[4]   Synthesis of poly(aryleneethynylene)s bearing glucose units as substituents [J].
Babudri, F ;
Colangiuli, D ;
Di Lorenzo, PA ;
Farinola, GM ;
Hassan Omar, O ;
Naso, F .
CHEMICAL COMMUNICATIONS, 2003, (01) :130-131
[5]   New approaches for decarboxylative biaryl coupling [J].
Baudoin, Olivier .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1373-1375
[6]   Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides [J].
Bilodeau, Francois ;
Brochu, Marie-Christine ;
Guimond, Nicolas ;
Thesen, Kris H. ;
Forgione, Pat .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1550-1560
[7]  
Bohlmann F., 1973, Naturally occurring acetylenes
[8]  
Breitenbach J., 1996, COMPREHENSIVE SUPRAM, V2, P29
[9]   Homocoupling reaction of terminal alkynes catalyzed by a reusable cationic 2,2′-bipyridyl palladium(II)/CuI system in water [J].
Chen, Shao-Nung ;
Wu, Wei-Yi ;
Tsai, Fu-Yu .
GREEN CHEMISTRY, 2009, 11 (02) :269-274
[10]  
CHODKIEWICZ W, 1957, CR HEBD ACAD SCI, V245, P322