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金(I)或三氯化镓催化炔烃的氢芳基化合成荧蒽。

Synthesis of fluoranthenes by hydroarylation of alkynes catalyzed by gold(I) or gallium trichloride.

机构信息

Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans 16, 43007 Tarragona, Spain.

出版信息

Beilstein J Org Chem. 2011;7:1520-5. doi: 10.3762/bjoc.7.178. Epub 2011 Nov 14.

DOI:10.3762/bjoc.7.178
PMID:22238527
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3252853/
Abstract

Electrophilic gold(I) catalyst 6 competes with GaCl(3) as the catalyst of choice in the synthesis of fluoranthenes by intramolecular hydroarylation of alkynes. The potential of this catalyst for the preparation of polyarenes is illustrated by a synthesis of two functionalized decacyclenes in a one-pot transformation in which three C-C bonds are formed with high efficiency.

摘要

亲电金(I)催化剂 6 在炔烃的分子内氢芳基化反应中与 GaCl(3)竞争,成为合成荧蒽类化合物的首选催化剂。该催化剂在多环芳烃的制备方面具有潜力,通过一锅法转化可以高效地形成三个 C-C 键,合成了两个功能化的十环癸二烯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/aaac08a5d39d/Beilstein_J_Org_Chem-07-1520-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/628472821bfc/Beilstein_J_Org_Chem-07-1520-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/3860addc2b09/Beilstein_J_Org_Chem-07-1520-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/a7f14a195719/Beilstein_J_Org_Chem-07-1520-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/5a0bffb322e5/Beilstein_J_Org_Chem-07-1520-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/aaac08a5d39d/Beilstein_J_Org_Chem-07-1520-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/628472821bfc/Beilstein_J_Org_Chem-07-1520-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/3860addc2b09/Beilstein_J_Org_Chem-07-1520-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/a7f14a195719/Beilstein_J_Org_Chem-07-1520-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/5a0bffb322e5/Beilstein_J_Org_Chem-07-1520-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b949/3252853/aaac08a5d39d/Beilstein_J_Org_Chem-07-1520-g006.jpg

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1
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Angew Chem Int Ed Engl. 2011 Jun 14;50(25):5762-5. doi: 10.1002/anie.201100989. Epub 2011 May 9.
3
A multipurpose gold(I) precatalyst.一种多用途金(I)前体催化剂。
Expeditious Green Synthesis of Novel 4-Methyl-1,2,5,6-tetraazafluoranthen-3(2)-one Analogue from Ninhydrin: N/S-Alkylation and Aza-Michael Addition.
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ACS Omega. 2020 Mar 3;5(10):5436-5442. doi: 10.1021/acsomega.0c00045. eCollection 2020 Mar 17.
4
Synthesis of Fluoranthene Derivatives via Tandem Suzuki-Miyaura and Intramolecular C-H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions.在均相和非均相催化条件下通过串联铃木-宫浦反应和分子内C-H芳基化反应合成荧蒽衍生物
ACS Omega. 2017 Dec 7;2(12):8689-8696. doi: 10.1021/acsomega.7b01566. eCollection 2017 Dec 31.
5
Anatomy of gold catalysts: facts and myths.金催化剂的剖析:事实与误解
Org Biomol Chem. 2015 Jul 14;13(26):7103-18. doi: 10.1039/c5ob00736d. Epub 2015 Jun 9.
6
Gold(I)-Catalyzed Activation of Alkynes for the Construction of Molecular Complexity.金(I)催化炔烃活化以构建分子复杂性。
Chem Rev. 2015 Sep 9;115(17):9028-72. doi: 10.1021/cr500691k. Epub 2015 Apr 6.
Chem Commun (Camb). 2011 May 7;47(17):4893-5. doi: 10.1039/c1cc10293a. Epub 2011 Mar 23.
4
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5
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J Nanosci Nanotechnol. 2008 Sep;8(9):4787-92. doi: 10.1166/jnn.2008.ic69.
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Gold(I)-catalyzed intermolecular addition of carbon nucleophiles to 1,5- and 1,6-enynes.金(I)催化的碳亲核试剂与1,5-和1,6-烯炔的分子间加成反应。
J Org Chem. 2008 Oct 3;73(19):7721-30. doi: 10.1021/jo8014769. Epub 2008 Aug 30.
10
Fullerenes from aromatic precursors by surface-catalysed cyclodehydrogenation.通过表面催化环脱氢反应由芳香族前体合成富勒烯。
Nature. 2008 Aug 14;454(7206):865-8. doi: 10.1038/nature07193.