Visible-Light Photocatalytic Bicyclization of 1,7-Enynes toward Functionalized Sulfone-Containing Benzo[a]fluoren-5-ones

被引：75

作者：

Huang, Min-Hua ^{[1
,2
]}

Zhu, Yi-Long ^{[1
,2
]}

Hao, Wen-Juan ^{[2
]}

Wang, Ai-Fang ^{[2
]}

Wang, De-Cai ^{[1
]}

Liu, Feng ^{[2
]}

Wei, Ping ^{[1
]}

Tu, Shu-Jiang ^{[2
]}

Jiang, Bo ^{[2
]}

机构：

[1] Nanjing Tech Univ, Biotechnol & Pharmaceut Engn, Nanjing 210009, Jiangsu, Peoples R China

[2] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 211116, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 13期

关键词：

arylsulfonylation; benzo[a] fluorenes; bicyclizations; 1,7-enynes; photocatalysis; BENZENE-TETHERED 1,7-ENYNES; PHOTOREDOX CATALYSIS; SULFINIC ACIDS; ELECTRON-TRANSFER; TERMINAL ALKYNES; EFFICIENT SYNTHESIS; 3,4-DIHYDROQUINOLIN-2(1H)-ONES; ORGANOCATALYSIS; CASCADE; DIFUNCTIONALIZATION;

D O I：

10.1002/adsc.201700124

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new visible-light photocatalytic arylsulfonylation and bicyclization of C(sp3)-tethered 1,7enynes with sulfinic acids has been developed, delivering functionalized sulfone-containing benzo[a]fluoren-5-ones with generally good yields. This Eosin Y-catalyzed approach makes use of visible light as a safe and eco-friendly energy source to drive cascade cyclization reactions, resulting in continuous multiple bond-forming events including CS and C-C bonds to efficiently construct polycycliclinked alkyl aryl sulfones.

引用

页码：2229 / 2234

页数：6

共 76 条

[1]

Amador A. G., 2016, ANGEW CHEM, V128, P2348

[2] A Chiral Metal Photocatalyst Architecture for Highly Enantioselective Photoreactions [J].

Amador, Adrian G. ;

Yoon, Tehshik P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (07) :2304-2306

[3] Synthesis of trifluoromethylated 3,4-dihydroquinolin-2(1H)-ones via a photo-induced radical cyclization of benzene-tethered 1,7-enynes with Togni reagent [J].

An, Yuanyuan ;

Kuang, Yunyan ;

Wu, Jie .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08) :994-998

[4] Recent synthetic additions to the visible light photoredox catalysis toolbox [J].

Angnes, Ricardo A. ;

Li, Zhou ;

Correia, Carlos Roque D. ;

Hammond, Gerald B. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (35) :9152-9167

[5]

[Anonymous], 2014, ANGEW CHEM, DOI DOI 10.1021/JA509383R

[6]

[Anonymous], 2014, ANGEW CHE, DOI DOI 10.1039/C4GC00542B

[7]

[Anonymous], 2014, ANGEW CHEM

[8]

[Anonymous], 2014, ANGEW CHEM

[9] 2-Sulfonyl-4-chloroanilino moiety: A potent pharmacophore for the anti-human immunodeficiency virus type 1 activity of pyrrolyl aryl sulfones [J].

Artico, M ;

Silvestri, R ;

Massa, S ;

Loi, AG ;

Corrias, S ;

Piras, G ;

LaColla, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (02) :522-530

[10] Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis [J].

Beatty, Joel W. ;

Stephenson, Corey R. J. .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1474-1484

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