Diarylrhodates as Promising Active Catalysts for the Arylation of Vinyl Ethers with Grignard Reagents

被引:58
作者
Iwasaki, Takanori [1 ]
Miyata, Yoshinori [1 ]
Akimoto, Ryo [1 ]
Fujli, Yuuld [1 ]
Kuniyasu, Hitoshi [1 ]
Kambe, Nobuaki [1 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词
CROSS-COUPLING REACTION; BOND-FORMING REACTIONS; CARBON-CARBON BONDS; X-RAY-STRUCTURE; ALKYL-HALIDES; ARYLBORONIC ACIDS; OXYGEN; 1,3-BUTADIENE; 1,4-ADDITION; TOSYLATES;
D O I
10.1021/ja5043534
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Anionic diarylrhodium complexes, generated by reacting [RhCl(cod)](2) with 2 equiv of aryl Grignard reagents, were found to be effective active catalysts in cross-coupling reactions of vinyl ethers with aryl Grignard reagents, giving rise to the production of vinyl arenes. In this catalytic system, vinyl-O bonds were preferably cleaved over Ar-O or Ar-Br bonds. A lithium rhodate complex was isolated, and its crystal structure was determined by X-ray crystallography.
引用
收藏
页码:9260 / 9263
页数:4
相关论文
共 51 条
[1]   Rhodium-Catalyzed Cleavage Reaction of Aryl Methyl Ethers with Thioesters [J].
Arisawa, Mieko ;
Nihei, Yuri ;
Suzuki, Takaaki ;
Yamaguchi, Masahiko .
ORGANIC LETTERS, 2012, 14 (03) :855-857
[2]  
Berthon G., 2010, Catalytic Asymmetric Conjugate Reactions
[3]   Synthetic applications of rhodium catalysed conjugate addition [J].
Edwards, Hannah J. ;
Hargrave, Jonathan D. ;
Penrose, Stephen D. ;
Frost, Christopher G. .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2093-2105
[4]  
Evans PA, 2005, MODERN RHODIUM-CATALYZED ORGANIC REACTIONS, P1, DOI 10.1002/3527604693
[5]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[6]   SYNTHESIS AND REACTIVITY OF MONONUCLEAR ANIONIC PENTAFLUOROPHENYL COMPOUNDS OF RHODIUM(I) AND IRIDIUM(I) - X-RAY STRUCTURE OF [(P(OPH)(3))(2)(C6F5)(2)RHAG(PPH(3))] [J].
GARCIA, MP ;
JIMENEZ, MV ;
LAHOZ, FJ ;
ORO, LA .
INORGANIC CHEMISTRY, 1995, 34 (08) :2153-2159
[7]   PARAMAGNETIC MONONUCLEAR RHODIUM(II) ORGANOMETALLIC COMPLEXES - X-RAY STRUCTURE OF [RH(C6CL5)2(P(OPH)3)2] [J].
GARCIA, MP ;
JIMENEZ, MV ;
ORO, LA ;
LAHOZ, FJ ;
CASAS, JM ;
ALONSO, PJ .
ORGANOMETALLICS, 1993, 12 (08) :3257-3263
[8]   Nickel-Catalyzed Coupling of Thiomethyl-Substituted 1,3-Benzothiazoles with Secondary Alkyl Grignard Reagents [J].
Ghaderi, Arash ;
Iwasaki, Takanori ;
Fukuoka, Asuka ;
Terao, Jun ;
Kambe, Nobuaki .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (09) :2951-2955
[9]  
Goossen L. J., 2009, ANGEW CHEM INT EDIT, V48, P2
[10]   Alternatives to Organoboron Reagents in Rhodium-Catalyzed Conjugate Additions [J].
Hargrave, Jonathan D. ;
Allen, Joseph C. ;
Frost, Christopher G. .
CHEMISTRY-AN ASIAN JOURNAL, 2010, 5 (03) :386-396