Cycloparaphenylenes via [2+2+2] cycloaddition

被引：16

作者：

Kohrs, Daniel ^{[1
,2
]}

Volkmann, Jannis ^{[1
,2
]}

Wegner, Hermann A. ^{[1
,2
]}

机构：

[1] Justus Liebig Univ Giessen, Inst Organ Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany

[2] Justus Liebig Univ Giessen, Ctr Mat Res ZfM LaMa, Heinrich Buff Ring 16, D-35392 Giessen, Germany

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 54期

关键词：

PHOTOPHYSICAL PROPERTIES; SIZE; CYCLOTRIMERIZATION;

D O I：

10.1039/d2cc02289c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The [2+2+2] cycloaddition (CA) offers great potential as an atom economic method for the formation of substituted aromatic rings. In this article, we highlight the application of this versatile method in synthetic approaches towards substituted cycloparaphenylenes (CPPs). The [2+2+2] CA can take over different tasks within the synthesis depending on the targeted CPP. These approaches were divided into three key steps: aromatization (which finalises the CPP), macrocyclization (the formation of a strain-reduced macrocycle) and the [2+2+2] CA. Based on this analysis the strategies were categorised into four classes based on which task the [2+2+2] CA fulfills. We point out the benefits and drawbacks of each synthesic strategy and summarize our findings to provide the reader with an easy insight into this research field.

引用

页码：7483 / 7494

页数：12

共 69 条

[1] A Strain Induced Change of Mechanism from a [2+2+2] to a [2+1+2+1] Cycloaddition Reaction [J].

Anne-Florence Tran-Van ;

Goetz, Silas ;

Neuburger, Markus ;

Wegner, Hermann A. .

ORGANIC LETTERS, 2014, 16 (09) :2410-2413

[2] Thieme Chemistry Journals Awardees - Where Are They Now? Aromaticity as a Source for Strain Energy? Synthesis of Curved Polycyclic Aromatic Structures via [2+2+2] Cycloaddition Reactions [J].

Beeck, Sebastian ;

Wegner, Hermann A. .

SYNLETT, 2017, 28 (09) :1018-1027

[3] A BN-Doped Cycloparaphenylene Debuts [J].

Chen, Min ;

Unikela, Kiran S. ;

Ramalakshmi, Rongala ;

Li, Bo ;

Darrigan, Clovis ;

Chrostowska, Anna ;

Liu, Shih-Yuan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (03) :1556-1560

[4] [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].

Chopade, Pramod R. ;

Louie, Janis .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327

[5] From an acyclic, polyunsaturated precursor to the polycyclic taxane ring system: The [4+2]/[2+2+2] and [2+2+2]/[4+2] cyclization strategies [J].

Chouraqui, G ;

Petit, M ;

Phansavath, P ;

Aubert, C ;

Malacria, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (06) :1413-1421

[6] Multifunctionalized octamethoxy-[8]cycloparaphenylene: facile synthesis and analysis of novel photophysical and photoinduced electron transfer properties [J].

Cui, Shengsheng ;

Zhuang, Guilin ;

Wang, Jinyi ;

Huang, Qiang ;

Wang, Shengda ;

Du, Pingwu .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (11) :1885-1890

[7] The dynamic, size-dependent properties of [5]-[12]cycloparaphenylenes [J].

Darzi, Evan R. ;

Jasti, Ramesh .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (18) :6401-6410

[8] Selective Syntheses of [7]-[12]Cycloparaphenylenes Using Orthogonal Suzuki-Miyaura Cross-Coupling Reactions [J].

Darzi, Evan R. ;

Sisto, Thomas J. ;

Jasti, Ramesh .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (15) :6624-6628

[9] Recent advances in [2+2+2] cycloaddition reactions [J].

Dominguez, Gema ;

Perez-Castells, Javier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3430-3444

[10]

Evans PJ, 2014, NAT CHEM, V6, P404, DOI [10.1038/NCHEM.1888, 10.1038/nchem.1888]

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