Combined C–H functionalization/O–H insertion reaction to form tertiary β-alkoxy substituted β-aminophosphonates catalyzed by [Cu(MeCN)4]PF6

Yan Cai; Yuchen Lu; Chengbin Yu; Hairong Lyu; Zhiwei Miao

doi:10.1039/C3OB40941D

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Combined C–H functionalization/O–H insertion reaction to form tertiary β-alkoxy substituted β-aminophosphonates catalyzed by [Cu(MeCN)₄]PF₆†‡

Yan Cai,^a Yuchen Lu,^a Chengbin Yu,^a Hairong Lyu^a and Zhiwei Miao*^ab

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* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
E-mail: miaozhiwei@nankai.edu.cn
Fax: +86 2350 2351
Tel: +86 2350 4783

^b Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Tsinghua University, Beijing 100084, China

Abstract

The copper-catalyzed C–H functionalization/O–H insertion reaction of α-diazophosphonates with alcohols has been developed with iodine as an additive. In order to understand this reaction, we present here a possible mechanism for the combined reaction. This process provides straightforward access to tertiary β-alkoxy substituted β-aminophosphonate derivatives with moderate to good yields.

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Article information

DOI: https://doi.org/10.1039/C3OB40941D
Article type: Paper
Submitted: 09 May 2013
Accepted: 02 Jul 2013
First published: 02 Jul 2013

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Org. Biomol. Chem., 2013,11, 5491-5499

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Combined C–H functionalization/O–H insertion reaction to form tertiary β-alkoxy substituted β-aminophosphonates catalyzed by [Cu(MeCN)₄]PF₆

Y. Cai, Y. Lu, C. Yu, H. Lyu and Z. Miao, Org. Biomol. Chem., 2013, 11, 5491 DOI: 10.1039/C3OB40941D

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Organic & Biomolecular Chemistry