GaCl3-catalyzed ortho-ethynylation reaction of N-benzylanilines

被引：56

作者：

Amemiya, R ^{[1
]}

Fujii, A ^{[1
]}

Yamaguchi, M ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Aoba Ku, Sendai, Miyagi 9808578, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 22期

基金：

日本学术振兴会;

关键词：

N-benzylaniline; ortho-ethynylation; gallium(III) chloride; chloroethyne; catalysis;

D O I：

10.1016/j.tetlet.2004.03.187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiated N-benzylanilines were ethynylated at the ortho-position with silylchloroethyne at 120 degreesC in the presence of a catalytic amount of GaCl3. Trimethylsilylated N-methylaniline could also be used for this transformation. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：4333 / 4335

页数：3

共 14 条

[1] Sequential carbometalation/elimination reaction takes place between gallium enolate and chloroethyne
Amemiya, R
Fujii, A
Arisawa, M
Yamaguchi, M
[J]. CHEMISTRY LETTERS, 2003, 32 (03) : 298 - 299
[2] GaCl3-catalyzed α-ethynylation reaction of silyl enol ethers
Amemiya, R
Fujii, A
Arisawa, M
Yamaguchi, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 686 (1-2) : 94 - 100
[3] One-step ethynylation of silyl enol ether with chlorosilylethyne
Arisawa, M
Amemiya, R
Yamaguchi, M
[J]. ORGANIC LETTERS, 2002, 4 (13) : 2209 - 2211
[4] Efficient reagents for the synthesis of 5-, 7-, and 5,7-substituted indoles starting from aromatic amines: Scope and limitations
Ezquerra, J
Pedregal, C
Lamas, C
Barluenga, J
Perez, M
GarciaMartin, MA
Gonzalez, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) : 5804 - 5812
[5] NUCLEOPHILIC AROMATIC-SUBSTITUTION BY ORGANO-ALUMINUM REAGENTS - APPLICATION TO THE SYNTHESIS OF INDOLES
FUJIWARA, J
FUKUTANI, Y
SANO, H
MARUOKA, K
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (24) : 7177 - 7179
[6] Efficient construction of indole rings from 2-ethynylaniline derivatives catalyzed by copper(II) salts and its application to the tandem cyclization reactions
Hiroya, K
Itoh, S
Ozawa, M
Kanamori, Y
Sakamoto, T
[J]. TETRAHEDRON LETTERS, 2002, 43 (07) : 1277 - 1280
[7] STUDIES OF REACTIONS OF AMINES WITH SULFUR-TRIOXIDE .8. INSERTION OF SULFUR-TRIOXIDE INTO THE N-SI BOND OF ANILINOTRIMETHYLSILANE - AN IMPROVED METHOD FOR THE PREPARATION OF FREE PHENYLAMIDOSULFURIC ACID
KANETANI, F
OKADA, E
NEGORO, K
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (08) : 2517 - 2520
[8] GaCl3-catalyzed ortho-ethynylation of phenols
Kobayashi, K
Arisawa, M
Yamaguchi, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (29) : 8528 - 8529
[9] Group VI metal-promoted endo-azacyclizations via alkyne-derived metal vinylidene carbenes
McDonald, FE
Chatterjee, AK
[J]. TETRAHEDRON LETTERS, 1997, 38 (44) : 7687 - 7690
[10] PALLADIUM-CATALYZED SYNTHESIS OF 2-SUBSTITUTED INDOLES
RUDISILL, DE
STILLE, JK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (25) : 5856 - 5866

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