Visible-Light-Mediated 1,7-Enyne Bicyclizations for Synthesis of Cyclopenta[c]quinolines and Benzo[j]phenanthridines

被引：88

作者：

Gao, Fei ^{[1
]}

Yang, Chao ^{[1
]}

Ma, Na ^{[1
]}

Gao, Guo-Lin ^{[1
]}

Li, Dazhi ^{[1
]}

Xia, Wujiong ^{[1
]}

机构：

[1] Harbin Inst Technol, Shenzhen Grad Sch, State Key Lab Urban Water Resource & Environm, Harbin 150080, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 03期

关键词：

PHOTOREDOX CATALYSIS; RADICAL CYCLIZATION; CYCLOISOMERIZATION; FUNCTIONALIZATION; 1,6-ENYNES; FLUORINE; ALKYLATION; N-ENYNES; ALKALOIDS; CASCADE;

D O I：

10.1021/acs.orglett.5b03662

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A photocatalytic process for 1,7-enyne bicyclizations with alpha-bromo diethyl malonate has been established via synergistic domino bicyclizations. This protocol provides an efficient and practical method for the synthesis of various cyclopenta[c]quinolines and benzo[j]phenanthridines under operational simplicity and mild reaction conditions.

引用

页码：600 / 603

页数：4

共 50 条

[1] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[2]

[Anonymous], 2015, ANGEW CHEM, V127, P9713

[3] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[4] 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

[5] Electrophilic activation and cycloisomerization of enynes: A new route to functional cyclopropanes [J].

Bruneau, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (16) :2328-2334

[6] Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].

Campbell, Michael G. ;

Ritter, Tobias .

CHEMICAL REVIEWS, 2015, 115 (02) :612-633

[7] CRYSTAL-STRUCTURE AND ABSOLUTE-CONFIGURATION OF (+)-SCANDINE HYDROBROMIDE [J].

CANNON, JR ;

CROFT, KD ;

MATSUKI, Y ;

PATRICK, VA ;

TOIA, RF ;

WHITE, AH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (08) :1655-1664

[8] Photoredox-Initiated α-Alkylation of Imines through a Three-Component Radical/Cationic Reaction [J].

Courant, Thibaut ;

Masson, Geraldine .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (02) :423-427

[9] Marrying Iterative Synthesis to Cascading Radical Cyclization: 6-endo/5-exo Radical Cascade across Bis-Vinyl Ethers [J].

Davies, Katherine A. ;

Wulff, Jeremy E. .

ORGANIC LETTERS, 2011, 13 (20) :5552-5555

[10] Tandem Cyclizations of 1,6-Enynes with Arylsulfonyl Chlorides by Using Visible-Light Photoredox Catalysis [J].

Deng, Guo-Bo ;

Wang, Zhi-Qiang ;

Xia, Jia-Dong ;

Qian, Peng-Cheng ;

Song, Ren-Jie ;

Hu, Ming ;

Gong, Lu-Bin ;

Li, Jin-Heng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1535-1538

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