Copper-catalyzed three-component phosphorylation-peroxidation of alkenes

被引：34

作者：

Chen, Yan ^{[1
]}

Chen, Yuanjin ^{[1
]}

Lu, Shenglin ^{[1
]}

Li, Zhiping ^{[1
]}

机构：

[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 06期

基金：

美国国家科学基金会;

关键词：

P-H COMPOUNDS; CARBONYLATION-PEROXIDATION; UNACTIVATED ALKENES; ALPHA; BETA-UNSATURATED ESTERS; RADICAL-ADDITION; NATURAL-PRODUCTS; P(O)-H COMPOUNDS; SINGLET OXYGEN; BOND FORMATION; T-HYDRO;

D O I：

10.1039/c7qo01045a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A copper-catalyzed phosphorylation-peroxidation of alkenes has been developed. The three-component protocol provides practical access to multisubstituted -phosphoryl peroxides by the reactions of P(O)-H compounds, alkenes and tert-butyl hydroperoxide (TBHP). The obtained -phosphoryl peroxides can be applied to the synthesis of -phosphoryl epoxides by using lithium bis(trimethylsilyl)amide (LHMDS) as a base.

引用

页码：972 / 976

页数：5

共 70 条

[41] Ruthenium catalyzed biomimetic oxidation in organic synthesis inspired by cytochrome P-450 [J].

Murahashi, Shun-Ichi ;

Zhang, Dazhi .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (08) :1490-1501

[42] Formally Copper(III)-Alkylperoxo Complexes as Models of Possible Intermediates in Monooxygenase Enzymes [J].

Neisen, Benjamin D. ;

Gagnon, Nicole L. ;

Dhar, Debanjan ;

Spaeth, Andrew D. ;

Tolman, William B. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (30) :10220-10223

[43] Generation, Characterization, and Reactivity of a CuII-Alkylperoxide/Anilino Radical Complex: Insight into the O-O Bond Cleavage Mechanism [J].

Paria, Sayantan ;

Ohta, Takehiro ;

Morimoto, Yuma ;

Ogura, Takashi ;

Sugimoto, Hideki ;

Fujieda, Nobutaka ;

Goto, Kei ;

Asano, Kaori ;

Suzuki, Takeyuki ;

Itoh, Shinobu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (34) :10870-10873

[44] Knowledge of the proposed chemical mechanism of action and cytochrome P450 metabolism of antimalarial trioxanes like artemisinin allows rational design of new antimalarial peroxides [J].

Posner, GH ;

O'Neill, PM .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (06) :397-404

[45] Stabilization of Two Radicals with One Metal: A Stepwise Coupling Model for Copper-Catalyzed Radical-Radical Cross-Coupling [J].

Qi, Xiaotian ;

Zhu, Lei ;

Bai, Ruopeng ;

Lan, Yu .

SCIENTIFIC REPORTS, 2017, 7

[46] Surface Modification Using Phosphonic Acids and Esters [J].

Queffelec, Clemence ;

Petit, Marc ;

Janvier, Pascal ;

Knight, D. Andrew ;

Bujoli, Bruno .

CHEMICAL REVIEWS, 2012, 112 (07) :3777-3807

[47]

Rappoport Z., 2006, CHEM PEROXIDES, V2

[48] Measurements of peroxides and what they tell us [J].

Reeves, CE ;

Penkett, SA .

CHEMICAL REVIEWS, 2003, 103 (12) :5199-5218

[49] Acid-Catalyzed Oxidative Radical Addition of Ketones to Olefins [J].

Schweitzer-Chaput, Bertrand ;

Demaerel, Joachim ;

Engler, Hauke ;

Klussmann, Martin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) :8737-8740

[50] Bioactive natural products with carbon-phosphorus bonds and their biosynthesis [J].

Seto, H ;

Kuzuyama, T .

NATURAL PRODUCT REPORTS, 1999, 16 (05) :589-596

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