Synthesis of functionalized malononitriles via Fe-catalysed hydrogen atom transfers of alkenes

被引：2

作者：

Zhu, Tianxiang ^{[1
]}

Zhang, Xue-Jun ^{[2
]}

Zhou, Zihan ^{[1
]}

Xu, Zitong ^{[1
]}

Ma, Mengtao ^{[1
]}

Zhao, Binlin ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Sci, Dept Chem & Mat Sci, Nanjing 210037, Peoples R China

[2] Southeast Univ, Zhongda Hosp, Sch Med, Dept Orthoped Surg, Nanjing, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 07期

基金：

中国国家自然科学基金;

关键词：

UNACTIVATED OLEFINS; RADICAL REACTIONS; HANTZSCH ESTERS; REDUCING AGENT; METAL; BOND; IRON; PHOTOCATALYSIS; AZIRIDINATION; ALKYLATION;

D O I：

10.1039/d1ob02332b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Described herein is a practical and convenient approach that enabled radical-mediated conjugate addition of unreactive alkenes to electron-deficient alkenes leading to a broad range of substituted malononitriles. These reactions are believed to proceed by Fe-catalysed hydrogen atom transfer (HAT) onto the alkenes affording carbon-centered radical intermediates with Markovnikov selectivity, followed by the capture of electron-deficient alkenes. We explored this synthesis approach under mild conditions with high efficiency and broad substrate scope and the utility is highlighted by the further synthetic transformations of the obtained substituted malononitriles.

引用

页码：1480 / 1487

页数：8

共 61 条

[21] Base-Promoted Cascade Approach for the Preparation of Reduced Knoevenagel Adducts Using Hantzsch Esters as Reducing Agent in Water [J].

He, Tao ;

Shi, Ronghua ;

Gong, Yimou ;

Jiang, Guangyou ;

Liu, Ming ;

Qian, Shan ;

Wang, Zhouyu .

SYNLETT, 2016, 27 (12) :1864-1869

[22] Simple, Chemoselective Hydrogenation with Thermodynamic Stereocontrol [J].

Iwasaki, Kotaro ;

Wan, Kanny K. ;

Oppedisano, Alberto ;

Crossley, Steven W. M. ;

Shenvi, Ryan A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (04) :1300-1303

[23] Light-Promoted Bromine-Radical-Mediated Selective Alkylation and Amination of Unactivated C(sp3)-H Bonds [J].

Jia, Penghao ;

Li, Qingyao ;

Poh, Wei Chuen ;

Jiang, Heming ;

Liu, Haiwang ;

Deng, Hongping ;

Wu, Jie .

CHEM, 2020, 6 (07) :1766-1776

[24] Hydrogenation of Alkenes via Cooperative Hydrogen Atom Transfer [J].

Kattamuri, Padmanabha, V ;

West, Julian G. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (45) :19316-19326

[25] Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources [J].

Kirby, Georgina ;

Grimaud, Laurence ;

Vitale, Maxime R. ;

Prestat, Guillaume ;

Berhal, Farouk .

GREEN CHEMISTRY, 2021, 23 (23) :9428-9432

[26] Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides [J].

Kuo, Jonathan L. ;

Hartung, John ;

Han, Arthur ;

Norton, Jack R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (03) :1036-1039

[27] C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow [J].

Laudadio, Gabriele ;

Deng, Yuchao ;

van der Wal, Klaas ;

Ravelli, Davide ;

Nuno, Manuel ;

Fagnoni, Maurizio ;

Guthrie, Duncan ;

Sun, Yuhan ;

Noel, Timothy .

SCIENCE, 2020, 369 (6499) :92-+

[28] Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2 [J].

Li, Jing ;

Lear, Martin J. ;

Hayashi, Yujiro .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (31) :9060-9064

[29] Nano-K2CO3: preparation, characterization and evaluation of reactive activities [J].

Li, Jun-Zhang ;

Fan, Shi-Ming ;

Sun, Xuan-Fei ;

Liu, Shouxin .

RSC ADVANCES, 2016, 6 (03) :1865-1869

[30] Wacker-Type Oxidation Using an Iron Catalyst and Ambient Air: Application to Late-Stage Oxidation of Complex Molecules [J].

Liu, Binbin ;

Jin, Fengli ;

Wang, Tianjiao ;

Yuan, Xiaorong ;

Han, Wei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (41) :12712-12717

← 1 2 3 4 5 6 7 →