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

[1] Synthesis, characterization and unusual near-infrared luminescence of 1,1,4,4-tetracyanobutadiene derivatives [J].

Bui, Anh Thy ;

Philippe, Clotilde ;

Beau, Maxime ;

Richy, Nicolas ;

Cordier, Marie ;

Roisnel, Thierry ;

Lemiegre, Loic ;

Mongin, Olivier ;

Paul, Frederic ;

Trolez, Yann .

CHEMICAL COMMUNICATIONS, 2020, 56 (24) :3571-3574

[2] Visible Light Uranyl Photocatalysis: Direct C-H to C-C Bond Conversion [J].

Capaldo, Luca ;

Merli, Daniele ;

Fagnoni, Maurizio ;

Ravelli, Davide .

ACS CATALYSIS, 2019, 9 (04) :3054-3058

[3] Unusually weak metal-hydrogen bonds in HV(CO)4(P-P) and their effectiveness as H• donors [J].

Choi, Jongwook ;

Pulling, Mary E. ;

Smith, Deborah M. ;

Norton, Jack R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (13) :4250-+

[4] Fe-Catalyzed Aziridination Is Governed by the Electron Affinity of the Active Imido-Iron Species [J].

Coin, Guillaume ;

Patra, Ranjan ;

Rana, Sujoy ;

Biswas, Jyoti Prasad ;

Dubourdeaux, Patrick ;

Clemancey, Martin ;

de Visser, Sam P. ;

Maiti, Debabrata ;

Maldivi, Pascale ;

Latour, Jean-Marc .

ACS CATALYSIS, 2020, 10 (17) :10010-10020

[5] Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins [J].

Crossley, Steven W. M. ;

Obradors, Carla ;

Martinez, Ruben M. ;

Shenvi, Ryan A. .

CHEMICAL REVIEWS, 2016, 116 (15) :8912-9000

[6] Aziridination of alkenes promoted by iron or ruthenium complexes [J].

Damiano, Caterina ;

Intrieri, Daniela ;

Gallo, Emma .

INORGANICA CHIMICA ACTA, 2018, 470 :51-67

[7]

Dao H.T., 2014, J AM CHEM SOC, V136, P1300

[8] Microtubing-Reactor-Assisted Aliphatic C-H Functionalization with HCl as a Hydrogen-Atom-Transfer Catalyst Precursor in Conjunction with an Organic Photoredox Catalyst [J].

Deng, Hong-Ping ;

Zhou, Quan ;

Wu, Jie .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (39) :12661-12665

[9] PHASE-TRANSFER CATALYSIS WITHOUT SOLVENT - SELECTIVE MONOALKYLATION OR DIALKYLATION OF MALONONITRILE [J].

DIEZBARRA, E ;

DELAHOZ, A ;

MORENO, A ;

SANCHEZVERDU, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (10) :2589-2592

[10] Sodium borohydride as the only reagent for the efficient reductive alkylation of malononitrile with ketones and aldehydes [J].

Dunham, JC ;

Richardson, AD ;

Sammelson, RE .

SYNTHESIS-STUTTGART, 2006, (04) :680-686

← 1 2 3 4 5 6 7 →