Synthesis of Cationic [4], [5], and [6]Azahelicenes with Extended π-Conjugated Systems

被引：3

作者：

Hruby, Samuel ^{[1
]}

Ulc, Jan ^{[1
]}

Cisarova, Ivana ^{[2
]}

Kotora, Martin ^{[1
]}

机构：

[1] Charles Univ Prague, Fac Sci, Dept Organ Chem, Hlavova 8, Prague 12843, Czech Republic

[2] Charles Univ Prague, Fac Sci, Dept Inorgan Chem, Hlavova 8, Prague 12843, Czech Republic

来源：

CATALYSTS | 2023年 / 13卷 / 05期

关键词：

C-C bond activation; C-H bond activation; helicenes; catalysis; rhodium; fluorescence; ONE-POT SYNTHESIS; ONE HUNDRED YEARS; C-H ACTIVATION; PHOTOPHYSICAL PROPERTIES; PHENANTHRIDINES; ROUTE; CONSTRUCTION; BIPHENYLENE; DERIVATIVES; COMPLEXES;

D O I：

10.3390/catal13050912

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The scope of Rh-catalyzed C-C bond cleavage/annulation of biphenylene with various aromatic nitriles was studied. The subsequent Rh- and Ir-catalyzed C-H bond activation/annulation sequence of the formed 9-arylphenanthridines with alkynes gave rise to cationic [4], [5], [6] helical quinolizinium salts. The scope of the reaction with respect to the structural features of the starting 9-arylphenanthridines and alkynes was studied. Their helical arrangement was confirmed through single-crystal X-ray analyses of selected compounds. Most of the prepared quinolizinium salts exhibited fluorescence emission maxima in the region of 525-623 nm with absolute quantum yields up to 25%.

引用

页数：12

共 46 条

[21] S-shaped para-Quinodimethane-Embedded Double [6]Helicene and Its Charged Species Showing Open-Shell Diradical Character [J].

Jiang, Qing ;

Han, Yi ;

Zou, Ya ;

Phan, Hoa ;

Yuan, Liu ;

Herng, Tun Seng ;

Ding, Jun ;

Chi, Chunyan .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (67) :15613-15622

[22] Synthesis of Phenanthridines via a Rhodium-Catalyzed C-C Bond Cleavage Reaction of Biphenylene with Nitriles [J].

Korotvicka, Ales ;

Frejka, David ;

Hampejsova, Zuzana ;

Cisarova, Ivana ;

Kotora, Martin .

SYNTHESIS-STUTTGART, 2016, 48 (07) :987-996

[23] Caged cyclopropenes for controlling bioorthogonal reactivity [J].

Kumar, Pratik ;

Jiang, Ting ;

Li, Sining ;

Zainul, Omar ;

Laughlin, Scott T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (22) :4081-4085

[24] High-Valent Pentamethylcyclopentadienylcobalt(III) or -iridium(III)-Catalyzed CH Annulation with Alkynes: Synthesis of Heterocyclic Quaternary Ammonium Salts [J].

Lao, Ye-Xing ;

Zhang, Shang-Shi ;

Liu, Xu-Ge ;

Jiang, Chun-Yong ;

Wu, Jia-Qiang ;

Li, Qingjiang ;

Huang, Zhi-Shu ;

Wang, Honggen .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) :2186-2191

[25]

Lee D.H., 2010, KR Patent, Patent No. 2010007143

[26] An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp☆MCl2]2 (M = Rh, Ir) [J].

Li, Ling ;

Brennessel, William W. ;

Jones, William D. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12414-12419

[27] RhIII-Catalyzed C-H Activation: A Versatile Route towards Various Polycyclic Pyridinium Salts [J].

Luo, Ching-Zong ;

Gandeepan, Parthasarathy ;

Jayakumar, Jayachandran ;

Parthasarathy, Kanniyappan ;

Chang, Yu-Wei ;

Cheng, Chien-Hong .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (42) :14181-14186

[28] One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the Sonogashira coupling reaction [J].

Mio, MJ ;

Kopel, LC ;

Braun, JB ;

Gadzikwa, TL ;

Hull, KL ;

Brisbois, RG ;

Markworth, CJ ;

Grieco, PA .

ORGANIC LETTERS, 2002, 4 (19) :3199-3202

[29] NOVEL AROMATIC SYSTEMS .7. BENZO-CYCLOBUTADIENE AND DIBENZOCYCLOBUTADIENE DICATIONS [J].

OLAH, GA ;

LIANG, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (18) :6045-6049

[30] Photophysical properties of N-alkylated azahelicene derivatives as DNA intercalators: counterion effects [J].

Passeri, Rosita ;

Aloisi, Gian Gaetano ;

Elisei, Fausto ;

Latterini, Loredana ;

Caronna, Tullio ;

Fontana, Francesca ;

Natali Sora, Isabella .

PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2009, 8 (11) :1574-1582

← 1 2 3 4 5 →