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四(二甲氨基)乙烯（TDAE）还原芳基重氮盐：高效生成芳基自由基衍生产物。

Reduction of arenediazonium salts by tetrakis(dimethylamino)ethylene (TDAE): efficient formation of products derived from aryl radicals.

机构信息

WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295, Cathedral Street, Glasgow G1 1XL, UK.

出版信息

Beilstein J Org Chem. 2009;5:1. doi: 10.3762/bjoc.5.1. Epub 2009 Jan 12.

DOI:10.3762/bjoc.5.1
PMID:19259337
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2649425/
Abstract

Tetrakis(dimethylamino)ethylene (TDAE 1), has been exploited for the first time as a mild reagent for the reduction of arenediazonium salts to aryl radical intermediates through a single electron transfer (SET) pathway. Cyclization of the aryl radicals produced in this way led, in appropriate substrates, to syntheses of indolines and indoles. Cascade radical cyclizations of aryl radicals derived from arenediazonium salts are also reported. The relative ease of removal of the oxidized by-products of TDAE from the reaction mixture makes the methodology synthetically attractive.

摘要

四(二甲氨基)乙烯 (TDAE1) 首次被用作温和试剂，通过单电子转移 (SET) 途径将重氮盐还原为芳基自由基中间体。通过这种方式产生的芳基自由基环化，在适当的底物中，导致吲哚啉和吲哚的合成。还报道了芳基重氮盐衍生的芳基自由基的级联自由基环化。TDAE 的氧化副产物从反应混合物中去除相对容易，这使得该方法在合成上具有吸引力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/ca55ba180bc9/Beilstein_J_Org_Chem-05-01-g011.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/ef56b4e8f1c5/Beilstein_J_Org_Chem-05-01-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/d24f9f78027a/Beilstein_J_Org_Chem-05-01-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/aba29f10c80b/Beilstein_J_Org_Chem-05-01-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/3ef91ca2c52b/Beilstein_J_Org_Chem-05-01-g007.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/e37b54605d3b/Beilstein_J_Org_Chem-05-01-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/ca55ba180bc9/Beilstein_J_Org_Chem-05-01-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/b219d2e5b70d/Beilstein_J_Org_Chem-05-01-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/0da5db895b38/Beilstein_J_Org_Chem-05-01-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/ef56b4e8f1c5/Beilstein_J_Org_Chem-05-01-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/d24f9f78027a/Beilstein_J_Org_Chem-05-01-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/aba29f10c80b/Beilstein_J_Org_Chem-05-01-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/3ef91ca2c52b/Beilstein_J_Org_Chem-05-01-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/401ff8017cb8/Beilstein_J_Org_Chem-05-01-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/780591ebe47b/Beilstein_J_Org_Chem-05-01-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/e37b54605d3b/Beilstein_J_Org_Chem-05-01-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/be12/2649425/ca55ba180bc9/Beilstein_J_Org_Chem-05-01-g011.jpg

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1
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2
Studies toward the oxidative and reductive activation of C-S bonds in 2'--aryl-2'-thiouridine derivatives.关于2'-芳基-2'-硫代尿苷衍生物中碳-硫键氧化和还原活化的研究。
Tetrahedron. 2016 Apr 21;72(16):1969-1977. doi: 10.1016/j.tet.2016.02.063.
3
Functionalization of 6-nitrobenzo[1,3]dioxole with carbonyl compounds via TDAE methodology.通过TDAE方法实现6-硝基苯并[1,3]二氧杂环戊烯与羰基化合物的官能化反应。
Chem Commun (Camb). 2022 Jan 25;58(8):1100-1103. doi: 10.1039/d1cc05691c.
4
Probing the interaction between the encapsulated water molecule and the fullerene cages in HO@C and HO@CN.探究HO@C和HO@CN中被包裹水分子与富勒烯笼之间的相互作用。
Chem Sci. 2018 Jun 4;9(25):5666-5671. doi: 10.1039/c8sc01031e. eCollection 2018 Jul 7.
5
Fates of imine intermediates in radical cyclizations of N-sulfonylindoles and ene-sulfonamides.N-磺酰基吲哚和烯基磺酰胺自由基环化中亚胺中间体的命运。
Beilstein J Org Chem. 2015 Sep 17;11:1649-55. doi: 10.3762/bjoc.11.181. eCollection 2015.
6
Discovery and development of organic super-electron-donors.有机超电子给体的发现与发展。
J Org Chem. 2014 May 2;79(9):3731-46. doi: 10.1021/jo500071u. Epub 2014 Mar 25.
7
Metal-free reductive cleavage of C-N and S-N bonds by photoactivated electron transfer from a neutral organic donor.通过中性有机给体的光激活电子转移实现 C-N 和 S-N 键的无金属还原断裂。
Angew Chem Int Ed Engl. 2014 Jan 7;53(2):474-8. doi: 10.1002/anie.201306543. Epub 2013 Dec 6.
8
Radical cyclizations of cyclic ene sulfonamides occur with β-elimination of sulfonyl radicals to form polycyclic imines.环状烯基磺酰胺的自由基环化反应伴随着磺酰基自由基的β-消除，形成多环亚胺。
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5
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6
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