布朗斯特酸催化生成钯配合物：炔烃的高效头-尾二聚反应。
A Brønsted acid-catalyzed generation of palladium complexes: efficient head-to-tail dimerization of alkynes.
机构信息
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
出版信息
Chem Commun (Camb). 2013 Sep 4;49(68):7498-500. doi: 10.1039/c3cc43131b.
PMID:23852048
Abstract
A Brønsted acid Ph2P(O)OH can efficiently catalyze the reaction of a Pd(0) complex with an alkyne to produce a novel alkenyl(alkynyl)palladium complex via selective hydropalladation and ligand exchange processes. On the basis of this finding, an efficient Pd(0)/Ph2P(O)OH mediated head-to-tail dimerization of alkynes was disclosed.
摘要
布朗斯特酸 Ph2P(O)OH 可以有效地催化 Pd(0) 配合物与炔烃的反应，通过选择性的加氢钯化和配体交换过程，生成新型的烯基（炔基）钯配合物。基于这一发现，我们揭示了一种高效的 Pd(0)/Ph2P(O)OH 介导的炔烃的头尾二聚反应。
相似文献
1
A Brønsted acid-catalyzed generation of palladium complexes: efficient head-to-tail dimerization of alkynes.
Chem Commun (Camb). 2013 Sep 4;49(68):7498-500. doi: 10.1039/c3cc43131b.
2
Carboxylate switch between hydro- and carbopalladation pathways in regiodivergent dimerization of alkynes.
Chemistry. 2014 Jul 28;20(31):9578-88. doi: 10.1002/chem.201402809. Epub 2014 Jul 10.
3
General and selective head-to-head dimerization of terminal alkynes proceeding via hydropalladation pathway.
Org Lett. 2012 Jun 1;14(11):2846-9. doi: 10.1021/ol3010936. Epub 2012 May 16.
4
Palladium-catalyzed cross-coupling of electron-poor terminal alkynes with arylboronic acids under ligand-free and aerobic conditions.
J Org Chem. 2010 Aug 20;75(16):5635-42. doi: 10.1021/jo101063p.
5
Ligand and substrate effects during Pd-catalyzed cyclizations of alkyne-tethered cyclohexadienones.
Org Biomol Chem. 2013 Sep 14;11(34):5596-604. doi: 10.1039/c3ob27491h.
6
[2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands.
Angew Chem Int Ed Engl. 2005 Jul 25;44(30):4753-7. doi: 10.1002/anie.200500879.
7
Palladium-catalyzed desulfitative hydroarylation of alkynes with sodium sulfinates.
Chem Commun (Camb). 2013 Sep 4;49(68):7501-3. doi: 10.1039/c3cc43723j.
8
Let the best ring win: selective macrocycle formation through Pd-catalyzed or Cu-mediated alkyne homocoupling.
Angew Chem Int Ed Engl. 2004 Mar 19;43(13):1694-7. doi: 10.1002/anie.200353043.
9
Distannylation of strained carbon-carbon triple bonds catalyzed by a palladium complex.
Angew Chem Int Ed Engl. 2004 Sep 27;43(38):5052-5. doi: 10.1002/anie.200460189.
10
Palladium-catalyzed oxidative diarylating carbocyclization of enynes.
Org Lett. 2012 Jul 6;14(13):3538-41. doi: 10.1021/ol301551x. Epub 2012 Jun 20.
引用本文的文献
1
Synthesis of 1,3-Enynes by Iron-Catalyzed Propargylic C-H Functionalization: An Alkyne Analogue for the Eschenmoser Methenylation.
Org Lett. 2024 Apr 26;26(16):3355-3360. doi: 10.1021/acs.orglett.4c00696. Epub 2024 Apr 11.
2
-Hydroalkynylation of Internal 1,3-Enynes Enabled by Cooperative Catalysis.
J Am Chem Soc. 2023 Mar 15;145(10):5624-5630. doi: 10.1021/jacs.3c00514. Epub 2023 Mar 2.
3
Late 3d Metal-Catalyzed (Cross-) Dimerization of Terminal and Internal Alkynes.
Front Chem. 2021 Mar 11;9:635826. doi: 10.3389/fchem.2021.635826. eCollection 2021.
4
Ligand-Controlled Diastereoselective Cobalt-Catalysed Hydroalkynylation of Terminal Alkynes to E- or Z-1,3-Enynes.
Chemistry. 2020 Sep 21;26(53):12129-12133. doi: 10.1002/chem.202001697. Epub 2020 Sep 7.
5
Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3-Diynes.
Angew Chem Int Ed Engl. 2020 Jun 2;59(23):9032-9040. doi: 10.1002/anie.201915386. Epub 2020 Mar 18.
6
Transition metal-catalyzed couplings of alkynes to 1,3-enynes: modern methods and synthetic applications.
Chem Soc Rev. 2016 Apr 21;45(8):2212-38. doi: 10.1039/c5cs00892a. Epub 2016 Feb 1.
7
Mechanisms for the synthesis of conjugated enynes from diphenylacetylene and trimethylsilylacetylene catalyzed by a nickel(0) complex: DFT study of ligand-controlled selectivity.
J Mol Model. 2015 May;21(5):135. doi: 10.1007/s00894-015-2672-7. Epub 2015 May 3.
Zotero 插件