Unexpected high regiocontrol in Heck reaction of fluorine-containing electron-deficient olefins-Highly regio- and stereoselective synthesis of β-fluoroalkyl-α-aryl-α,β-unsaturated ketones

被引:13
作者
Konno, Tsutomu [1 ]
Yamada, Shigeyuki [1 ]
Tani, Akinori [1 ]
Nishida, Masataka [1 ]
Miyabe, Tomotsugu [1 ]
Ishihara, Takashi [1 ]
机构
[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan
关键词
Fluorine-containing alkenes; Heck reaction; Aryldiazonium salts; beta-Fluoroalkyl-alpha; beta-unsaturated ketones; Regioselective; Stereoselective; CONTAINING INTERNAL ACETYLENES; MICHAEL ADDITION-REACTIONS; 1,3-DIPOLAR CYCLOADDITION; ACID; ANALOGS; ALKYNES; CARBONS; ACCESS; ARYL;
D O I
10.1016/j.jfluchem.2009.07.002
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Treatment of (E)-4,4,4-trifluoro-1-aryl-2-buten-1-one with various aryldiazonium salts in the presence of palladium catalyst gave the corresponding alpha-arylated Heck adducts with high regio- and stereoselectivity in good to high yields. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:913 / 921
页数:9
相关论文
共 59 条
[51]   PM3 analysis of nitrone cycloadditions to methyl 4,4,4-trifluoro-2-butenoate [J].
Tanaka, K ;
Imase, T ;
Iwata, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1996, 69 (08) :2243-2248
[52]   REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF TRIFLUOROMETHYLATED ISOXAZOLIDINES BY 1,3-DIPOLAR CYCLOADDITION OF 1,1,1-TRIFLUORO-3-PHENYLSULFONYLPROPENE WITH NITRONES, AND THEIR CONVERSION INTO TRIFLUOROMETHYLATED SYN-3-AMINO ALCOHOLS [J].
TSUGE, H ;
OKANO, T ;
EGUCHI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (21) :2761-2766
[53]   Synthesis of terminal monofluoro olefins [J].
van Steenis, JH ;
van der Gen, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (19) :2117-2133
[54]   ADVANCES IN THE PREPARATION OF BIOLOGICALLY-ACTIVE ORGANOFLUORINE COMPOUNDS [J].
WELCH, JT .
TETRAHEDRON, 1987, 43 (14) :3123-3197
[55]   Electronically promoted payne rearrangement of 3-CF3-2,3-epoxyalcohols [J].
Yamazaki, T ;
Ichige, T ;
Kitazume, T .
ORGANIC LETTERS, 2004, 6 (22) :4073-4076
[56]   HIGHLY STEREOSELECTIVE ASYMMETRIC MICHAEL ADDITION-REACTIONS EMPLOYING (R-E)-3,3,3-TRIFLUOROPROP-1-ENYL PARA-TOLYL SULFOXIDE [J].
YAMAZAKI, T ;
ISHIKAWA, N ;
IWATSUBO, H ;
KITAZUME, T .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) :1340-1342
[57]   STEREOSELECTIVE MICHAEL ADDITION-REACTIONS OF ACYLATED OXAZOLIDINONES TO ETHYL 3-TRIFLUOROMETHYLACRYLATE [J].
YAMAZAKI, T ;
HAGA, J ;
KITAZUME, T .
CHEMISTRY LETTERS, 1991, (12) :2175-2178
[58]   Michael addition of organocopper species to 3-[(E)-4,4,4-trifluorobut-2-enoyl]oxazolin-2-ones [J].
Yamazaki, T ;
Shinohara, N ;
Kitazume, T ;
Sato, S .
JOURNAL OF FLUORINE CHEMISTRY, 1999, 97 (1-2) :91-96
[59]   MODIFIED PREPARATION METHOD OF TRIFLUOROMETHYLATED PROPARGYLIC ALCOHOLS AND ITS APPLICATION TO CHIRAL 2,6-DIDEOXY-6,6,6-TRIFLUOROSUGARS [J].
YAMAZAKI, T ;
MIZUTANI, K ;
KITAZUME, T .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (19) :6046-6056