Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts

被引：55

作者：

Lu, Shirong ^{[1
]}

Si, Weili ^{[1
]}

Bao, Ming ^{[2
]}

Yamamoto, Yoshinori ^{[1
,2
]}

Jin, Tienan ^{[1
]}

机构：

[1] Tohoku Univ, WPI Adv Inst Mat Res WPI AIMR, Sendai, Miyagi 9808577, Japan

[2] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

关键词：

CHEMISTRY; HYDROFULLERENES; DIMERIZATION; C-60; SULFONAMIDES; DERIVATIVES; CYCLIZATION; ACCEPTOR; WATER;

D O I：

10.1021/ol401876n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and highly selective Co-catalyzed radical cycloaddition of [60]fullerene with active dibromides for the synthesis of three-, five-, six-, and seven-membered carbocycle-fused fullerene monoadducts has been reported. The controlled experiments unambiguously disclosed that the reaction proceeds through the formation of a fullerene monoradical as a key intermediate.

引用

页码：4030 / 4033

页数：4

共 53 条

[11] An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions [J].

Filippone, Salvatore ;

Maroto, Enrique E. ;

Martin-Domenech, Angel ;

Suarez, Margarita ;

Martin, Nazario .

NATURE CHEMISTRY, 2009, 1 (07) :578-582

[12] Metal ion dependent fluorescence quenching in a crown ether bridged porphyrin-fullerene dyad [J].

Ghiggino, Kenneth P. ;

Hutchison, James A. ;

Islan, D. -M. Shatiqul ;

Araki, Yasuyuki ;

Ito, Osamu ;

Langford, Steven J. ;

Lau, Vei-Lin ;

Takezaki, Makoto .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2006, 5 (12) :1150-1153

[13] New Concepts and Applications in the Macromolecular Chemistry of Fullerenes [J].

Giacalone, Francesco ;

Martin, Nazario .

ADVANCED MATERIALS, 2010, 22 (38) :4220-4248

[14] Biradical intermediate in the [2+2] photocycloaddition of dienes and alkenes to [60]fullerene [J].

Hatzimarinaki, M ;

Roubelakis, MM ;

Orfanopoulos, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14182-14183

[15] Indene-C60 Bisadduct: A New Acceptor for High-Performance Polymer Solar Cells [J].

He, Youjun ;

Chen, Hsiang-Yu ;

Hou, Jianhui ;

Li, Yongfang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (04) :1377-1382

[16] Diels-Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60 [J].

Hudhomme, Patrick .

COMPTES RENDUS CHIMIE, 2006, 9 (7-8) :881-891

[17] Cobalt-catalyzed Heck-type reaction of alkyl halides with styrenes [J].

Ikeda, Y ;

Nakamura, T ;

Yorimitsu, H ;

Oshima, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6514-6515

[18] Functional fullerenes for organic photovoltaics [J].

Li, Chang-Zhi ;

Yip, Hin-Lap ;

Jen, Alex K. -Y. .

JOURNAL OF MATERIALS CHEMISTRY, 2012, 22 (10) :4161-4177

[19] Cycloaddition reactions of hydrofullerenes with cyano-substituted alkenes under basic conditions [J].

Li, YJ ;

Wang, GW ;

Li, JX ;

Liu, YC .

NEW JOURNAL OF CHEMISTRY, 2004, 28 (08) :1043-1047

[20] Synthesis of [60]Fullerene-Fused Tetrahydronaphthalene and Indane Derivatives via a Pathway Switched by Aluminum Chloride [J].

Liu, Tong-Xin ;

Li, Fa-Bao ;

Wang, Guan-Wu .

ORGANIC LETTERS, 2011, 13 (22) :6130-6133

← 1 2 3 4 5 6 →