Unusual [2+4] and [2+2] cycloadditions of arenes in the confined cavity of self-assembled cages

被引：206

作者：

Nishioka, Yuki ^{[1
]}

Yamaguchi, Takumi ^{[1
]}

Yoshizawa, Michito ^{[1
]}

Fujita, Makoto ^{[1
]}

机构：

[1] Univ Tokyo, Dept Appl Chem, Sch Engn,Bunkyo Ku, CREST,Japan Sci & Technol Agcy, Tokyo 1138656, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 22期

关键词：

D O I：

10.1021/ja071591x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unusual [2+4] and [2+2] cross-cycloadditions of arenes were efficiently promoted within a self-assembled coordination cage. For example, triphenylene underwent the Diels-Alder reaction with N-cyclohexylmaleimide in good yield in the confined cavity of the cage, despite its inertness under ordinary conditions. Syn-stereoselective photodimerization of pyrene and N-cyclohexylmaleimide was also carried out quantitatively within the cage. The structures of these cross adducts were confirmed by NMR and X-ray crystallographic analysis.

引用

收藏

页码：7000 / +

页数：3

相关论文

共 24 条

[1] Biomimetic reactions catalyzed by cyclodextrins and their derivatives [J].

Breslow, R ;

Dong, SD .

CHEMICAL REVIEWS, 1998, 98 (05) :1997-2011

[2]

BRYCESMITH D, 1961, CHEM IND-LONDON, P429

[3] Selectivity in an encapsulated cycloaddition reaction [J].

Chen, J ;

Rebek, J .

ORGANIC LETTERS, 2002, 4 (03) :327-329

[4] SYNTHESES OF CORONENE AND 1-2-7-8-DIBENZOCORONENE [J].

CLAR, E ;

ZANDER, M .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (NOV) :4616-4619

[5] Supramolecular catalysis of a unimolecular transformation: Aza-cope rearrangement within a self-assembled host [J].

Fiedler, D ;

Bergman, RG ;

Raymond, KN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (48) :6748-6751

[6] Dendrimers as photochemical reaction media. photochemical behavior of unimolecular and bimolecular reactions in water-soluble dendrimers [J].

Kaanumalle, LS ;

Ramesh, R ;

Maddipatla, VSNM ;

Nithyanandhan, J ;

Jayaraman, N ;

Ramamurthy, V .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :5062-5069

[7] Water-soluble dendrimers as photochemical reaction media: Chemical behavior of singlet and triplet radical pairs inside dendritic reaction cavities [J].

Kaanumalle, LS ;

Nithyanandhan, J ;

Pattabiraman, M ;

Jayaraman, N ;

Ramamurthy, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :8999-9006

[8] Diels-Alder reactions through reversible encapsulation [J].

Kang, JM ;

Hilmersson, G ;

Santamaría, J ;

Rebek, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3650-3656

[9] Acceleration of a Diels-Alder reaction by a self-assembled molecular capsule [J].

Kang, JM ;

Rebek, J .

NATURE, 1997, 385 (6611) :50-52

[10] Selective C-H bond activation by a supramolecular host-guest assembly [J].

Leung, DH ;

Fiedler, D ;

Bergman, RG ;

Raymond, KN .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (08) :963-966