Ligand-Free Synthesis of 1,4-Disubstituted-1,3-diynes by Iron/Copper Cocatalyzed Homocoupling of Terminal Alkynes

被引:15
作者
Wang, Peipei [1 ]
Liu, Xiaoyan [1 ]
Zhang, Songlin [1 ]
机构
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
catalysis; copper; iron; 1; 3-diyne; ligand-free; CATALYZED DIRECT ARYLATION; COUPLING REACTION; N-ARYLATION; IRON; EFFICIENT; DIMERIZATION; PANAXYTRIOL; CHLORIDE; SYSTEM; ARENES;
D O I
10.1002/cjoc.201200878
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient protocol for Fe/Cu cocatalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted-1,3-diynes was presented. The results showed that both CuBr and FeCl3 played crucial roles in the reaction. It is noteworthy that this protocol employs mild, efficient, aerobic and ligand free conditions. The alkynes, including aromatic, heteroaromatic and aliphatic alkynes, were transformed into the corresponding 1,3-diynes in good to excellent yields.
引用
收藏
页码:187 / 194
页数:8
相关论文
共 77 条
[51]   Pd-Catalyzed Decarboxylative Coupling of Propiolic Adds: One-Pot Synthesis of 1,4-Disubstituted 1,3-Diynes via Sonogashira-Homocoupling Sequence [J].
Park, Jihye ;
Park, Eonjeong ;
Kim, Aejin ;
Park, Seul-A ;
Lee, Youngil ;
Chi, Ki-Whan ;
Jung, Young Hoon ;
Kim, In Su .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) :2214-2219
[52]  
Plietker B, 2011, TOP ORGANOMETAL CHEM, V33, P1, DOI 10.1007/978-3-642-14670-1
[53]   Olefin cross-metathesis as a tool in natural product degradation. The stereochemistry of (+)-falcarindiol [J].
Ratnayake, AS ;
Hemscheidt, T .
ORGANIC LETTERS, 2002, 4 (26) :4667-4669
[54]   Iron(III) chloride in oxidative C-C coupling reactions [J].
Sarhan, Abdelwareth A. O. ;
Bolm, Carsten .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (09) :2730-2744
[55]   The Promise and Challenge of Iron-Catalyzed Cross Coupling [J].
Sherry, Benjamin D. ;
Fuerstner, Alois .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1500-1511
[56]   Synthesis of naturally occurring polyynes [J].
Shun, ALKS ;
Tykwinski, RR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1034-1057
[57]   Synthesis of polyacetylenic montiporic acids A and B [J].
Stefani, HA ;
Costa, IM ;
Zeni, G .
TETRAHEDRON LETTERS, 1999, 40 (52) :9215-9217
[58]   ALLYLAMINE DERIVATIVES - A NEW CLASS OF ACTIVE SUBSTANCES IN ANTIFUNGAL CHEMOTHERAPY [J].
STUTZ, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04) :320-328
[59]  
TAILLEFER M, 2007, ANGEW CHEM, V119, P952
[60]   Efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles [J].
Taillefer, Marc ;
Xia, Ning ;
Ouali, Armelle .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :934-936