Visible light-induced one-pot synthesis of CF3/CF2-substituted cyclobutene derivatives

被引：10

作者：

Hu, Xiao ^{[1
]}

Ding, Aishun ^{[1
]}

Xu, Dawen ^{[1
,2
]}

Guo, Hao ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, 2005 Songhu Rd, Shanghai 200438, Peoples R China

[2] Zhuhai Fudan Innovat Inst, Zhuhai 519000, Guangdong, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 60期

关键词：

2+2; PHOTOCYCLOADDITION;

D O I：

10.1039/d1cc02696h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient one-pot approach for the controllable synthesis of trifluoromethyl/gem-difluoromethylene substituted cyclobutene derivatives has been developed. The mechanism may involve visible light-induced [2+2]-cycloaddition of quinolinones with 1-bromo-1-trifluoromethylethene, followed by base-promoted dehydrobromination, [1,3]-H shift and further dehydrofluorination. A variety of CF3/CF2-substituted cyclobutenes that are currently difficult to obtain are afforded in good yields in this protocol, which may find its way into future fluorinated cyclobutene preparation.

引用

页码：7441 / 7444

页数：4

共 29 条

[1] [2+2] Photocycloaddition of 3-Alkenyloxy-2-cycloalkenones: Enantioselective Lewis Acid Catalysis and Ring Expansion [J].

Brimioulle, Richard ;

Bach, Thorsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (47) :12921-12924

[2] Fluoroalkyl-Containing 1,2-Disubstituted Cyclobutanes: Advanced Building Blocks for Medicinal Chemistry [J].

Demchuk, Oleksandr P. ;

Hryshchuk, Oleksandr V. ;

Vashchenko, Bohdan V. ;

Trofymchuk, Serhii A. ;

Melnykov, Kostiantyn P. ;

Skreminskiy, Artem ;

Volochnyuk, Dmitriy M. ;

Grygorenko, Oleksandr O. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (01) :87-95

[3] REACTIVITY AND STEREOCHEMICAL STUDIES OF THE [2 + 2] CYCLO-ADDITION OF 1,1-DIFLUOROALLENE AND STYRENE [J].

DOLBIER, WR ;

WICKS, GE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3626-3631

[4] 2,2-difluorovinyl benzoates for diverse synthesis of gem-difluoroenol ethers by Ni-catalyzed cross-coupling reactions [J].

Du, Bingnan ;

Chan, Chun-Ming ;

Lee, Pui-Yiu ;

Cheung, Leong-Hung ;

Xu, Xin ;

Lin, Zhenyang ;

Yu, Wing-Yiu .

NATURE COMMUNICATIONS, 2021, 12 (01)

[5] FLUOROKETENES .4. CYCLOADDUCTS OF BIS(TRIFLUOROMETHYL)KETENE WITH ACETYLENES [J].

ENGLAND, DC ;

KRESPAN, CG .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (10) :3308-&

[6]

Fischer R., 2009, PCT Int. Appl.,, Patent No. [WO 2009019219 A2, 2009019219]

[7] Synthesis of Purine Nucleosides Built on a 3-Oxabicyclo[3.2.0]heptane Scaffold [J].

Flores, Ramon ;

Rustullet, Albert ;

Alibes, Ramon ;

Alvarez-Larena, Angel ;

de March, Pedro ;

Figueredo, Marta ;

Font, Josep .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13) :5369-5383

[8] Substituted cyclobutenes, their preparation, and their versatility in synthesis [J].

Gauvry, Noelle ;

Lescop, Cyrille ;

Huet, Francois .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (23) :5207-5218

[9] Cyclobutane carboxamide inhibitors of fungal melanin: Biosynthesis and their evaluation as fungicides [J].

Jennings, LD ;

Rayner, DR ;

Jordan, DB ;

Okonya, JF ;

Basarab, GS ;

Amorose, DK ;

Anaclerio, BM ;

Lee, JK ;

Schwartz, RS ;

Whitmore, KA .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (05) :897-907

[10] Copper-Catalyzed Trifluoromethylation of Alkyl Bromides [J].

Kornfilt, David J. P. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (17) :6853-6858

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