Ruthenium-Catalyzed ortho-Alkenylation of Phenylphosphine Oxides through Regio- and Stereoselective Alkyne Insertion into C-H Bonds

被引:72
作者
Itoh, Masaki [1 ]
Hashimoto, Yuto [1 ]
Hirano, Koji [1 ]
Satoh, Tetsuya [1 ,2 ]
Miura, Masahiro [1 ]
机构
[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
[2] JST, ACT C, Kawaguchi, Saitama 3320012, Japan
关键词
CHIRAL PHOSPHINE OXIDE; ALDOL REACTION; ARYL HALIDES; FUNCTIONALIZATION; ACTIVATION; REDUCTION; ARENES; HYDROARYLATION; ALLYLATION; COMPLEXES;
D O I
10.1021/jo401393b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct ortho-substitution took place efficiently upon treatment of tri-, di-, and monoarylphosphine oxides with internal alkynes in the presence of a ruthenium catalyst to produce (o-alkenylphenyl)phosphine oxides regio- and stereo-selectively. Chemoselective reduction of a product gave the corresponding (o-alkenylphenyl)phosphine, which may be useful as a ligand for transition metals.
引用
收藏
页码:8098 / 8104
页数:7
相关论文
共 79 条
[1]   Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Althammer, Andreas .
ORGANIC LETTERS, 2008, 10 (11) :2299-2302
[2]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[3]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[4]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[5]   Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles [J].
Anderson, Kevin W. ;
Tundel, Rachel E. ;
Ikawa, Takashi ;
Altman, Ryan A. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6523-6527
[6]   Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst [J].
Aoki, Shohei ;
Kotani, Shunsuke ;
Sugiura, Masaharu ;
Nakajima, Makoto .
CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5524-5526
[7]   Diethyl carbonate as a solvent for ruthenium catalysed C-H bond functionalisation [J].
Arockiam, Percia ;
Poirier, Valentin ;
Fischmeister, Cedric ;
Bruneau, Christian ;
Dixneuf, Pierre H. .
GREEN CHEMISTRY, 2009, 11 (11) :1871-1875
[8]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[9]   Palladium-catalysed synthesis of biaryl phosphines [J].
Baillie, C ;
Xiao, JL .
TETRAHEDRON, 2004, 60 (19) :4159-4168
[10]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365