The functionalization of a cascade of C(sp2)-H/C(sp3)-H bonds: synthesis of fused dihydropyrazoles via visible-light photoredox catalysis

被引：38

作者：

Cheng, Jian ^{[1
]}

Xu, Pan ^{[1
]}

Li, Weipeng ^{[1
]}

Cheng, Yixiang ^{[1
]}

Zhu, Chengjian ^{[1
,2
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210023, Jiangsu, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 80期

基金：

中国国家自然科学基金;

关键词：

PHOTOCATALYTIC GENERATION; DUAL CATALYSIS; STRATEGY; DIFLUOROALKYLATION; CYCLIZATION; DISCOVERY; ARYLATION; RADICALS; AMINES;

D O I：

10.1039/c6cc06410h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The functionalization of a cascade of C(sp(2))-H/C(sp(3))-H bonds in aldehyde hydrazones with simple 2,2-dibromo-1,3-dicarbonyls was achieved via visible-light photoredox catalysis. This method, which involves free radical addition, polar crossover and 6 pi electrocyclic reaction, provides an efficient approach for the synthesis of complex fused dihydropyrazoles and related derivatives with moderate to good yields and excellent regioselectivity under mild reaction conditions.

引用

页码：11901 / 11904

页数：4

共 57 条

[11] Kinesin spindle protein (KSP) inhibitors. Part 7: Design and synthesis of 3,3-disubstituted dihydropyrazolobenzoxazines as potent inhibitors of the mitotic kinesin KSP [J].

Garbaccio, Robert M. ;

Tasbera, Edward S. ;

Neilson, Lou Anne ;

Coleman, Paul J. ;

Fraley, Mark E. ;

Olson, Christy ;

Bergman, Jeff ;

Torrent, Maricel ;

Buser, Carolyn A. ;

Rickert, Keith ;

Walsh, Eileen S. ;

Hamilton, Kelly ;

Lobell, Robert B. ;

Tao, Weikang ;

South, Vicki J. ;

Diehl, Ronald E. ;

Davide, Joseph P. ;

Yan, Youwei ;

Kuo, Lawrence C. ;

Li, Chunze ;

Prueksaritanont, Thomayant ;

Fernandez-Metzler, Carmen ;

Mahan, Elizabeth A. ;

Slaughter, Donald E. ;

Salata, Joseph J. ;

Kohl, Nancy E. ;

Huber, Hans E. ;

Hartman, George D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (20) :5671-5676

[12] A CATALYTIC DEHYDROGENATION ROUTE TO AZOMETHINE IMINES [J].

GRIGG, R ;

HEANEY, F ;

IDLE, J ;

SOMASUNDERAM, A .

TETRAHEDRON LETTERS, 1990, 31 (19) :2767-2770

[13] Visible-Light-Induced Radical Tandem Aryldifluoroacetylation of Cinnamamides: Access to Difluoroacetylated Quinolone-2-ones And 1-Azaspiro[4.5]decanes [J].

Gu, Zhangxi ;

Zhang, Honglin ;

Xu, Pan ;

Cheng, Yixiang ;

Zhu, Chengjian .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (14-15) :3057-3063

[14] Discovery of Pyrroloaminopyrazoles as Novel PAK Inhibitors [J].

Guo, Chuangxing ;

McAlpine, Indrawan ;

Zhang, Junhu ;

Knighton, Daniel D. ;

Kephart, Susan ;

Johnson, M. Catherine ;

Li, Haitao ;

Bouzida, Djamal ;

Yang, Anle ;

Dong, Liming ;

Marakovits, Joseph ;

Tikhe, Jayashree ;

Richardson, Paul ;

Guo, Lisa C. ;

Kania, Robert ;

Edwards, Martin P. ;

Kraynov, Eugenia ;

Christensen, James ;

Piraino, Joseph ;

Lee, Joseph ;

Dagostino, Eleanor ;

Del-Carmen, Christine ;

Deng, Ya-Li ;

Smeal, Tod ;

Murray, Brion W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (10) :4728-4739

[15] C ∼ H Bond Functionalization through Intramolecular Hydride Transfer** [J].

Haibach, Michael C. ;

Seidel, Daniel .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) :5010-5036

[16] Exploratory synthetic studies of the alpha-methoxylation of amides via cuprous ion-promoted decomposition of o-diazobenzamides [J].

Han, G ;

LaPorte, MG ;

McIntosh, MC ;

Weinreb, SM ;

Parvez, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9483-9493

[17] Photodegradable Supramolecular Hydrogels with Fluorescence Turn-On Reporter for Photomodulation of Cellular Microenvironments [J].

He, Mingtao ;

Li, Jinbo ;

Tan, Subee ;

Wang, Ruzhi ;

Zhang, Yan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (50) :18718-18721

[18] Dual Catalysis Sees the Light: Combining Photoredox with Organo-, Acid, and Transition-Metal Catalysis [J].

Hopkinson, Matthew N. ;

Sahoo, Basudev ;

Li, Jun-Long ;

Glorius, Frank .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (14) :3874-3886

[19] The chemistry of amine radical cations produced by visible light photoredox catalysis [J].

Hu, Jie ;

Wang, Jiang ;

Nguyen, Theresa H. ;

Zheng, Nan .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :1977-2001

[20] Photocatalytic Generation of N-Centered Hydrazonyl Radicals: A Strategy for Hydroamination of β,γ-Unsaturated Hydrazones [J].

Hu, Xiao-Qiang ;

Chen, Jia-Rong ;

Wei, Qiang ;

Liu, Feng-Lei ;

Deng, Qiao-Hui ;

Beauchemin, Andre M. ;

Xiao, Wen-Jing .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) :12163-12167

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