含磷亚基化合物与未活化不饱和烃加成反应的最新进展：通过氢膦酰化及相关过程形成碳-磷键
Recent Developments in the Addition of Phosphinylidene-Containing Compounds to Unactivated Unsaturated Hydrocarbons: Phosphorus-Carbon Bond-Formation via Hydrophosphinylation and Related Processes.
作者信息
Coudray Laëtitia, Montchamp Jean-Luc
机构信息
Department of Chemistry, Box 298860, Texas Christian University, Fort Worth, Texas 76129 (USA).
出版信息
European J Org Chem. 2008 Jul 1;2008(21):3601-3613. doi: 10.1002/ejoc.200800331.
Abstract
The reactions of phosphinylidene-containing compounds with unactivated unsaturated hydrocarbons are reviewed. The review is organized by phosphorus-containing functional group types. Free-radical and metal-catalyzed additions of R(1)R(2)P(O)H to alkenes, alkynes, and related compounds, deliver functionalized organophosphorus compounds RP(O)R(1)R(2), including H-phosphinates, phosphinates, tertiary phosphine oxides, and phosphonates. The review covers the literature up to February 2008.
摘要
本文综述了含磷叶立德化合物与未活化不饱和烃的反应。综述按含磷官能团类型进行组织。R(1)R(2)P(O)H对烯烃、炔烃及相关化合物的自由基加成和金属催化加成反应，生成了官能化的有机磷化合物RP(O)R(1)R(2)，包括次膦酸酯、膦酸酯、叔膦氧化物和膦酸酯。本综述涵盖了截至2008年2月的文献。
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本文引用的文献
1
Palladium-catalyzed reactions of hypophosphorous compounds with allenes, dienes, and allylic electrophiles: methodology for the synthesis of allylic h-phosphinates.
J Org Chem. 2008 Mar 21;73(6):2292-301. doi: 10.1021/jo702542a. Epub 2008 Feb 15.
2
Palladium-catalyzed dehydrogenative cis double phosphorylation of alkynes with H-phosphonate leading to (Z)-bisphosphoryl-1-alkenes.
J Am Chem Soc. 2008 Mar 5;130(9):2752-3. doi: 10.1021/ja7108272. Epub 2008 Feb 8.
3
A novel approach to phosphonic acids from hypophosphorous acid.
Tetrahedron Lett. 2007 Aug 13;48(33):5755-5759. doi: 10.1016/j.tetlet.2007.06.090.
4
Methoden der Organischen Chemie (Houben-Weyl).
Science. 1964 May 8;144(3619):702-3. doi: 10.1126/science.144.3619.702-b.
5
Copper-catalyzed addition of H-phosphine oxides to alkynes forming alkenylphosphine oxides.
Chem Commun (Camb). 2007 Jan 21(3):272-4. doi: 10.1039/b613416e. Epub 2006 Oct 25.
6
Air-induced anti-Markovnikov addition of secondary phosphine oxides and H-phosphinates to alkenes.
Org Lett. 2007 Jan 4;9(1):53-5. doi: 10.1021/ol062505l.
7
Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols.
Org Lett. 2006 Aug 31;8(18):4169-71. doi: 10.1021/ol061828e.
8
Palladium-catalyzed asymmetric hydrophosphorylation of norbornenes.
Org Lett. 2006 May 11;8(10):2099-101. doi: 10.1021/ol060568y.
9
Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-gamma-[psiP(O)(OH)]-glutarate, a potent inhibitor of folylpoly-gamma-glutamate synthetase: synthesis and hydrolytic stability.
J Med Chem. 2006 Jan 26;49(2):770-88. doi: 10.1021/jm050871p.
10
Radical reaction of sodium hypophosphite with terminal alkynes: synthesis of 1,1-bis-H-phosphinates.
Org Lett. 2005 Dec 22;7(26):5909-12. doi: 10.1021/ol052533o.
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