用于固体负载底物上多键二酰亚胺还原的改进方法。
Improved method for the diimide reduction of multiple bonds on solid-supported substrates.
作者信息
Buszek Keith R, Brown Neil
机构信息
Department of Chemistry, Kansas State University, 111 Willard Hall, Manhattan, Kansas 66506, USA.
出版信息
J Org Chem. 2007 Apr 13;72(8):3125-8. doi: 10.1021/jo0622173. Epub 2007 Mar 17.
Abstract
A mild and improved method for reducing multiple bonds on various resins with diimide is described. The simple procedure readily generates diimide from 2-nitrobenzenesulfonohydrazide and triethylamine at room temperature. A number of representative multiple bonds in various steric and electronic environments were examined, including polar double bonds such as carbonyl and azo, for ease and selectivity of reduction. A general trend of reactivity was identified which revealed, inter alia, that terminal olefins, 1,2-disubstituted olefins, electron-poor olefins, and terminal alkynes were the most easily reduced.
摘要
描述了一种温和且改进的用二酰亚胺还原各种树脂上多重键的方法。该简单程序在室温下能由2-硝基苯磺酰肼和三乙胺轻松生成二酰亚胺。研究了各种空间和电子环境中的许多代表性多重键，包括羰基和偶氮等极性双键，以考察还原的难易程度和选择性。确定了一种一般的反应活性趋势，尤其表明末端烯烃、1,2-二取代烯烃、缺电子烯烃和末端炔烃最容易被还原。
相似文献
1
Improved method for the diimide reduction of multiple bonds on solid-supported substrates.
J Org Chem. 2007 Apr 13;72(8):3125-8. doi: 10.1021/jo0622173. Epub 2007 Mar 17.
2
Reduction of solid-supported olefins and alkynes.
J Org Chem. 2009 Dec 18;74(24):9535-8. doi: 10.1021/jo901764u.
3
Aerobic reduction of olefins by in situ generation of diimide with synthetic flavin catalysts.
Chemistry. 2011 May 16;17(21):5908-20. doi: 10.1002/chem.201003278. Epub 2011 Apr 14.
4
Ti-Catalyzed Multicomponent Oxidative Carboamination of Alkynes with Alkenes and Diazenes.
J Am Chem Soc. 2016 Nov 9;138(44):14570-14573. doi: 10.1021/jacs.6b09939. Epub 2016 Oct 28.
5
Organocatalytic diimide reduction of enamides in water.
Chem Commun (Camb). 2011 Jan 7;47(1):280-2. doi: 10.1039/c0cc02272a. Epub 2010 Aug 16.
6
Synthesis of trans-disubstituted alkenes by cobalt-catalyzed reductive coupling of terminal alkynes with activated alkenes.
Chemistry. 2012 Sep 10;18(37):11771-7. doi: 10.1002/chem.201200779. Epub 2012 Aug 2.
7
At the frontier between heterogeneous and homogeneous catalysis: hydrogenation of olefins and alkynes with soluble iron nanoparticles.
Dalton Trans. 2010 Sep 28;39(36):8464-71. doi: 10.1039/c0dt00177e. Epub 2010 Aug 13.
8
A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes.
Nat Chem. 2013 Aug;5(8):718-23. doi: 10.1038/nchem.1693. Epub 2013 Jul 7.
9
Flavin-catalyzed generation of diimide: an environmentally friendly method for the aerobic hydrogenation of olefins.
J Am Chem Soc. 2005 Oct 26;127(42):14544-5. doi: 10.1021/ja053976q.
10
More than bystanders: the effect of olefins on transition-metal-catalyzed cross-coupling reactions.
Angew Chem Int Ed Engl. 2008;47(5):840-71. doi: 10.1002/anie.200700278.
引用本文的文献
1
Assembling the carbon skeleton of A-74528.
Chem Sci. 2022 Jul 5;13(28):8395-8400. doi: 10.1039/d2sc01366e. eCollection 2022 Jul 20.
2
Chirality-driven self-assembly: application toward renewable/exchangeable resin-immobilized catalysts.
Org Biomol Chem. 2022 Jun 1;20(21):4314-4319. doi: 10.1039/d2ob00439a.
3
A Pot-Economical Approach to the Total Synthesis of Sch-725674.
Org Lett. 2016 Feb 5;18(3):516-9. doi: 10.1021/acs.orglett.5b03547. Epub 2016 Jan 13.
4
Synthetic Studies to Lyngbouilloside: A Phosphate Tether-Mediated Synthesis of the Macrolactone Core.
Tetrahedron Lett. 2015 Jun 3;56(23):3330-3333. doi: 10.1016/j.tetlet.2015.01.109.
5
Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles.
Biopolymers. 2015 Nov;104(6):663-73. doi: 10.1002/bip.22698.
6
A modular phosphate tether-mediated divergent strategy to complex polyols.
Beilstein J Org Chem. 2014 Oct 7;10:2332-2337. doi: 10.3762/bjoc.10.242. eCollection 2014.
7
One-pot isomerization-cross metathesis-reduction (ICMR) synthesis of lipophilic tetrapeptides.
ACS Comb Sci. 2014 Jul 14;16(7):342-51. doi: 10.1021/co500020a. Epub 2014 Jun 18.
8
9
An efficient, modular approach for the synthesis of (+)-strictifolione and a related natural product.
Org Lett. 2014 Jan 3;16(1):122-5. doi: 10.1021/ol403110p. Epub 2013 Dec 2.
10
Antitumor effects of synthetic 6,7-annulated-4-substituted indole compounds in L1210 leukemic cells in vitro.
Anticancer Res. 2012 Nov;32(11):4671-84.
本文引用的文献
1
Comprehensive survey of combinatorial library synthesis: 2004.
J Comb Chem. 2005 Nov-Dec;7(6):739-98. doi: 10.1021/cc050082t.
2
Multipolymer solution-phase reactions: application to the Mitsunobu reaction.
J Am Chem Soc. 2005 Jan 12;127(1):52-3. doi: 10.1021/ja045188r.
3
Enantioselective synthesis of 2-deoxy- and 2,3-dideoxyhexoses.
Org Lett. 2002 May 16;4(10):1771-4. doi: 10.1021/ol025844x.
4
Preparation of the Reagent o-Nitrobenzenesulfonylhydrazide.
J Org Chem. 1997 Oct 17;62(21):7507. doi: 10.1021/jo9710137.
5
Antitumor activity of novel octalactin A analogs in murine leukemia cells in vitro.
Anticancer Res. 1998 Jan-Feb;18(1A):97-106.
Zotero 插件