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通过氧化C-H官能化和环化反应实现银介导的中氮茚合成

Silver-Mediated Synthesis of Indolizines via Oxidative C-H functionalization and cyclization.

作者信息

Pandya Amit N, Fletcher James T, Villa Eric M, Agrawal Devendra K

机构信息

Department of Biomedical Sciences, Creighton University School of Medicine, Omaha, NE 68178, USA.

Department of Chemistry, Creighton University, Omaha, NE 68178, USA Tel: (402) 280 2938;

出版信息

Tetrahedron Lett. 2014 Dec 10;55(50):6922-6924. doi: 10.1016/j.tetlet.2014.10.112.

Abstract

An efficient strategy for the synthesis of indolizines from readily available starting materials via oxidative C-H functionalization and cyclization in one step has been demonstrated. This protocol represents wide substrate scope, high functional group tolerance and selectivity. The structure of the product was confirmed by the X-ray crystallographic studies. The AgCO required of this tandem reaction can be recycled and reused after undergoing oxidative reaction.

摘要

已经证明了一种通过氧化C-H官能化和环化一步从容易获得的起始原料合成中氮茚的有效策略。该方案具有广泛的底物范围、高官能团耐受性和选择性。产物的结构通过X射线晶体学研究得到证实。该串联反应所需的AgCO在经过氧化反应后可以回收再利用。

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The cross-dehydrogenative coupling of C(sp3)-H bonds: a versatile strategy for C-C bond formations.
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):74-100. doi: 10.1002/anie.201304268. Epub 2013 Nov 8.
5
Silver-mediated oxidative C-H/P-H functionalization: an efficient route for the synthesis of benzo[b]phosphole oxides.
J Am Chem Soc. 2013 Nov 13;135(45):16754-7. doi: 10.1021/ja407373g. Epub 2013 Oct 30.
6
Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.
Angew Chem Int Ed Engl. 2012 Oct 8;51(41):10236-54. doi: 10.1002/anie.201203269. Epub 2012 Sep 20.
8
C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.
Angew Chem Int Ed Engl. 2012 Sep 3;51(36):8960-9009. doi: 10.1002/anie.201201666. Epub 2012 Aug 6.
9
Pd-catalyzed C-3 functionalization of indolizines via C-H bond cleavage.
Org Biomol Chem. 2012 Sep 21;10(35):7108-19. doi: 10.1039/c2ob25643f. Epub 2012 Aug 7.
10
From C(sp2)-H to C(sp3)-H: systematic studies on transition metal-catalyzed oxidative C-C formation.
Chem Soc Rev. 2012 Sep 7;41(17):5588-98. doi: 10.1039/c2cs35096c. Epub 2012 Jul 10.

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