Synthesis of Belt- and Mobius-Shaped Cycloparaphenylenes by Rhodium-Catalyzed Alkyne Cyclotrimerization

被引：87

作者：

Nishigaki, Shuhei ^{[1
]}

Shibata, Yu ^{[1
]}

Nakajima, Atsuya ^{[2
]}

Okajima, Hajime ^{[2
]}

Masumoto, Yui ^{[3
]}

Osawa, Taisei ^{[3
]}

Muranaka, Atsuya ^{[4
]}

Sugiyama, Haruki ^{[5
]}

Horikawa, Ayano ^{[5
]}

Uekusa, Hidehiro ^{[5
]}

Koshino, Hiroyuki ^{[6
]}

Uchiyama, Masanobu ^{[3
,4
]}

Sakamoto, Akira ^{[2
]}

Tanaka, Ken ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Sci & Engn, Meguro Ku, Tokyo 1528550, Japan

[2] Aoyama Gakuin Univ, Dept Chem & Biol Sci, Chuo Ku, Sagamihara, Kanagawa 2525258, Japan

[3] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, 7-3-1 Hongo, Tokyo 1130033, Japan

[4] RIKEN, Adv Elements Chem Lab, CPR, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

[5] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528550, Japan

[6] RIKEN Ctr Sustainable Resource Sci CSRS, Mol Struct Characterizat Unit, 2-1 Hirosawa, Wako, Saitama 3510198, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 38期

关键词：

REGIOSELECTIVE INTERMOLECULAR CYCLOTRIMERIZATION; EXPANDED PORPHYRIN; AROMATICITY; COMPLEXES; NUMBER;

D O I：

10.1021/jacs.9b06197

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A belt-shaped [8] cycloparaphenylene (CPP) and an enantioenriched Mobius-shaped [10]CPP have been synthesized by high-yielding rhodium-catalyzed intramolecular cyclotrimerizations of a cyclic dodecayne and a pentadecayne, respectively. This Mobius-shaped [10]CPP possesses stable chirality and isolated with high enantiomeric purity. It is evident from the reaction Gibbs energy calculation that the above irreversible cyclotrimerizations are highly exothermic; therefore establishing that the intramolecular alkyne cyclotrimerization is a powerful route to strained cyclic molecular strips.

引用

页码：14955 / 14960

页数：6

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