Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

被引:114
作者
Gaertner, Dominik [1 ]
Stein, Andre Luiz [1 ]
Grupe, Sabine [1 ]
Arp, Johannes [1 ]
Jacobi von Wangelin, Axel [1 ]
机构
[1] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany
关键词
alkenes; cross-coupling; enols; Grignard reaction; iron catalysis; C-O ACTIVATION; ARYL; FE; NI; REAGENTS; ARYLMAGNESIUM; CONSTRUCTION; CLEAVAGE;
D O I
10.1002/anie.201504524
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Stable CO linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong CO bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 degrees C, 2h) with a ligand-free catalyst (1-2mol%).
引用
收藏
页码:10545 / 10549
页数:5
相关论文
共 64 条
[1]   Iron-Catalyzed Coupling of Aryl Sulfannates and Aryl/Vinyl Tosylates with Aryl Grignards [J].
Agrawal, Toolika ;
Cook, Silas P. .
ORGANIC LETTERS, 2014, 16 (19) :5080-5083
[2]   DIBENZO[A,E]CYCLOOCTATETRAENE IN A PROPOSED TEST FOR HETEROGENEITY IN CATALYSTS FORMED FROM SOLUBLE PLATINUM GROUP METAL-COMPLEXES [J].
ANTON, DR ;
CRABTREE, RH .
ORGANOMETALLICS, 1983, 2 (07) :855-859
[3]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[4]  
Astruc D., 2005, Angew. Chem, V117, P8062, DOI DOI 10.1002/ange.200500766
[5]   How Low Does Iron Go? Chasing the Active Species in Fe-Catalyzed Cross-Coupling Reactions [J].
Bedford, Robin B. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1485-1493
[6]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[7]  
Bullock R.M., 2010, Catalysis Without Precious Metals
[8]  
Cahiez G, 1998, SYNTHESIS-STUTTGART, P1199
[9]   Cu-catalyzed alkylation and Fe-catalyzed alkenylation of organomanganese reagents [J].
Cahiez, G ;
Marquais, S .
PURE AND APPLIED CHEMISTRY, 1996, 68 (01) :53-60
[10]  
Carey F.A., 1990, Advanced Organic Chemistry Part A: Structure and Mechanisms, V3