Reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride. Part 2: The Friedel-Crafts allylation and cyclopropylation of electron-rich aromatic compounds

被引：9

作者：

Kirihara, Masayuki

Noguchi, Takuya

Kakuda, Hiroko

Akimoto, Tatsuhiro

Shimajiri, Akihiro

Morishita, Minori

Hatano, Akihiko

Hirai, Yoshiro

机构：

[1] Shizuoka Inst Sci & Technol, Dept Mat & Life Sci, Shizuoka 4378555, Japan

[2] Toyama Univ, Fac Sci, Dept Chem, Toyama 9308555, Japan

[3] Toyama Univ, Chem Lab, Fac Med, Toyama 9300194, Japan

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 22期

关键词：

cyclopropyl silyl ether; diethylaminosulfur trifluoride; Friedel-Crafts allylation; Friedel-Crafts cyclopropylation;

D O I：

10.1016/j.tetlet.2006.03.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of tertiary cyclopropyl silyl ethers with diethylaminosulfur trifluoride in electron-rich aromatic Compounds causes the Friedel-Crafts alkylation to produce allylated or cyclopropylated aromatic compounds. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3777 / 3780

页数：4

共 8 条

[1] Friedel-Crafts reaction of dimethyl 2-oxopropylphosphonate and diethyl 2,2-diethoxyethylphosphonate with electron-rich arenes
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PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2005, 180 (12) : 2709 - 2715
[2] The catalytic Friedel-Crafts alkylation reaction of aromatic compounds with benzyl or allyl silyl ethers using Cl2Si(OTf)2 or Hf(OTf)4
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[3] Room temperature Mgl2-catalyzed Friedel-Crafts reaction between electron-rich (het)arenes and ethyl glyoxylate
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[4] Highly regioselective Friedel-Crafts reactions of electron-rich aromatic compounds with pyruvate catalyzed by Lewis acid-base: Efficient synthesis of pesticide cycloprothrin
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[5] Lewis Acid Catalyzed Friedel-Crafts Alkylation of Indoles and Other Electron-Rich Aromatic Compounds with Ethyl 2-(Diethoxyphos-phoyl) acrylate and Tetraethyl Ethene-1,1-diylbis(phosphonate)
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SYNTHESIS-STUTTGART, 2017, 49 (07): : 1689 - 1701
[6] A convenient method for the synthesis of 4,4-diarylbut-1-enes via the successive allylation of aromatic aldehydes and the Friedel-Crafts alkylation reaction of aromatic nucleophiles with the intermediary benzyl silyl ethers using HfCl4 or Cl2Si(OTf)2
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Suzuki, M
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TETRAHEDRON LETTERS, 2002, 43 (36) : 6395 - 6398
[7] Trifluoromethanesulfonic acid mediated Friedel-Crafts reaction of (E)-3-aryl-2-(diethoxyphosphoryl)acrylic acids with electron-rich hydroxyarenes.: A convenient approach to α-methylene-δ-valerolactones
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[8] Regioselective Friedel-Crafts Reaction of Electron-Rich Benzenoid Arenes and Spiroepoxyoxindole at the Spiro-Centre: Efficient Synthesis of Benzofuroindolines and 2H-Spiro[benzofuran]-3,3′-oxindoles
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