钛催化的炔烃与烯烃和重氮化合物的多组分氧化碳氨化反应。
Ti-Catalyzed Multicomponent Oxidative Carboamination of Alkynes with Alkenes and Diazenes.
机构信息
Department of Chemistry, University of Minnesota-Twin Cities , 207 Pleasant Street SE, Minneapolis, Minnesota 55455, United States.
出版信息
J Am Chem Soc. 2016 Nov 9;138(44):14570-14573. doi: 10.1021/jacs.6b09939. Epub 2016 Oct 28.
Abstract
The inter- or intramolecular oxidative carboamination of alkynes catalyzed by [pyTiClNPh] is reported. These multicomponent reactions couple alkenes, alkynes and diazenes to form either α,β-unsaturated imines or α-(iminomethyl)cyclopropanes via a Ti/Ti redox cycle. Each of these products is formed from a common azatitanacyclohexene intermediate that undergoes either β-H elimination or α,γ-coupling, wherein the selectivity is under substrate control.
摘要
报道了 [pyTiClNPh] 催化的炔烃的分子间或分子内氧化碳氨化反应。这些多组分反应通过 Ti/Ti 氧化还原循环将烯烃、炔烃和重氮化合物偶联，形成α,β-不饱和亚胺或α-(亚氨基甲基)环丙烷。这些产物中的每一个都是由一个共同的氮杂钛杂环戊烯中间体形成的，该中间体经历β-H 消除或α,γ-偶联，其中选择性受底物控制。
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本文引用的文献
1
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Nat Chem. 2016 Jan;8(1):63-8. doi: 10.1038/nchem.2386. Epub 2015 Nov 2.
2
Rhodium-catalysed syn-carboamination of alkenes via a transient directing group.通过瞬态导向基团实现铑催化的烯烃顺式碳胺化反应
Nature. 2015 Nov 5;527(7576):86-90. doi: 10.1038/nature15691. Epub 2015 Oct 21.
3
Titanium-catalyzed multicomponent couplings: efficient one-pot syntheses of nitrogen heterocycles.钛催化的多组分偶联反应：氮杂环的高效一锅合成法。
Acc Chem Res. 2015 Nov 17;48(11):2822-33. doi: 10.1021/acs.accounts.5b00280. Epub 2015 Aug 21.
4
Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.通过钯催化的炔烃碳胺化反应合成取代的2-氨基咪唑。在preclathridine天然产物合成中的应用。
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5
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Org Lett. 2011 Mar 4;13(5):1206-9. doi: 10.1021/ol200090g. Epub 2011 Feb 4.
6
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ChemMedChem. 2010 Mar 1;5(3):351-6. doi: 10.1002/cmdc.200900499.
7
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Chem Soc Rev. 2009 Nov;38(11):3051-60. doi: 10.1039/b901245c. Epub 2009 Jul 10.
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