Gallium trichloride-catalyzed exhaustive α-ethynylation reaction of 1-silylacetylenes

被引:10
作者
Amemiya, Ryo [1 ]
Yamaguchi, Masahiko [1 ]
机构
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
关键词
deprotonation; 1,4-enynes; ethynylation; gallium trichloride; propargylgallium; 1-silylacetylenes;
D O I
10.1002/adsc.200600399
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Gallium trichloride (GaCl3) catalyzes the ethynylation reaction of a 1,4-enyne with chlorosilyl-acetylene at the propargyl position giving a triethynylvinylmethane. This catalytic method can be applied to the exhaustive alpha-ethynylation of 1-silylacetylenes possessing less acidic propargyl protons, and mono-, di-, and triethynylated products are obtained depending on the structure of the starting materials.
引用
收藏
页码:1011 / 1014
页数:4
相关论文
共 29 条
[1]   GaCl3 in organic synthesis [J].
Amemiya, R ;
Yamaguchi, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (24) :5145-5150
[2]   One-step synthesis of triethynylvinylmethanes and tetraethynylmethanes by GaCl3-promoted diethynylation of 1,4-enynes and 1,4-diynes [J].
Amemiya, R ;
Suwa, K ;
Toriyama, J ;
Nishimura, Y ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (23) :8252-8253
[3]   GaCl3-catalyzed ortho-ethynylation reaction of N-benzylanilines [J].
Amemiya, R ;
Fujii, A ;
Yamaguchi, M .
TETRAHEDRON LETTERS, 2004, 45 (22) :4333-4335
[4]   GaCl3-catalyzed α-ethynylation reaction of silyl enol ethers [J].
Amemiya, R ;
Fujii, A ;
Arisawa, M ;
Yamaguchi, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 686 (1-2) :94-100
[5]  
BRANDSMA L, 1981, SYNTHESIS ACETYLENES, pCH3
[6]   REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF ALLENIC AND ACETYLENIC DERIVATIVES - ORGANOTITANIUM AND BORON REAGENTS [J].
FURUTA, K ;
ISHIGURO, M ;
HARUTA, R ;
IKEDA, N ;
YAMAMOTO, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (10) :2768-2776
[7]   ORGANOLANTHANIDE-CATALYZED CYCLODIMERIZATIONS OF DISUBSTITUTED ALKYNES [J].
HEERES, HJ ;
HEERES, A ;
TEUBEN, JH .
ORGANOMETALLICS, 1990, 9 (05) :1508-1510
[8]  
HOFFMAN TP, 2003, TETRAHEDRON, V59, P8913
[9]   PROPARGYLIC TITANIUM REAGENTS - REGIOCONTROLLED AND STEREOCONTROLLED SYNTHESIS OF ALLENIC AND ACETYLENIC ALCOHOLS [J].
ISHIGURO, M ;
IKEDA, N ;
YAMAMOTO, H .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (11) :2225-2227
[10]   Palladium acetic acid catalyzed allylation of some pronucleophiles with simple alkynes [J].
Kadota, I ;
Shibuya, A ;
Gyoung, YS ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (39) :10262-10263