Metal-Carbene-Templated Photochemistry in Solution: A Universal Route towards Cyclobutane Derivatives

被引：25

作者：

Li, Yang ^{[1
]}

Jin, Guang-Feng ^{[1
]}

An, Yuan-Yuan ^{[1
]}

Das, Rajorshi ^{[1
]}

Han, Ying-Feng ^{[1
]}

机构：

[1] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Xian 710127, Shaanxi, Peoples R China

来源：

CHINESE JOURNAL OF CHEMISTRY | 2019年 / 37卷 / 11期

基金：

中国国家自然科学基金;

关键词：

DICARBENE-DERIVED METALLACYCLES; SINGLE-CRYSTAL TRANSFORMATION; 2+2 PHOTODIMERIZATION; ORGANOMETALLIC MACROCYCLES; SUPRAMOLECULAR CONTROL; DIRECTED SYNTHESIS; PI INTERACTIONS; CYCLOADDITION; REACTIVITY; COMPLEX;

D O I：

10.1002/cjoc.201900348

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Summary of main observation and conclusion A series of dicarbene-bridged metallacycles [Ag-2(1)(2)](PF6)(2), [Ag-2(2)(2)](BF4)(2), [Ag-2(3)(2)](PF6)(2), [Ag-2(7)(2)](BF4)(2), [Ag-2(8)(2)](BF4)(2) and [Ag-2(11)(2)](PF6)(2) were obtained in high yields via the reactions of 1,2,4-triazole-, 1,2,3-triazole- and imidazo[1,5-a]pyridine-based ligands with Ag2O in CH3CN. The C=C double bonds in all of the newly synthesized metallacycles went through [2 + 2] photodimerization under UV irradiation condition (lambda = 365 nm, T = 298 K) yielding the dinuclear rctt-cyclobutane-silver(I) complexes [Ag-2(4)](PF6)(2), [Ag-2(5)](BF4)(2), [Ag-2(6)](PF6)(2), [Ag-2(9)](BF4)(2), [Ag-2(10)](BF4)(2) and [Ag-2(12)](PF6)(2), respectively with quantitative yields. Treatment of the these cyclobutane-bridged silver(I) complexes with NH4Cl resulted in the exclusive formation of cyclobutane derivatives after removal of the silver(I) metal ions.

引用

页码：1147 / 1152

页数：6

共 68 条

[1] A Bis-benzopyrroloisoquinoline Alkaloid Incorporating a Cyclobutane Core and a Chlorophenanthroindolizidine Alkaloid with Cytotoxic Activity from Ficus fistulosa var. tengerensis [J].

Al-Khdhairawi, Amjad Ayad Qatran ;

Krishnan, Premanand ;

Mai, Chun-Wai ;

Chung, Felicia Fei-Lei ;

Leong, Chee-Onn ;

Yong, Kien-Thai ;

Chong, Kam-Weng ;

Low, Yun-Yee ;

Kam, Toh-Seok ;

Lim, Kuan-Hon .

JOURNAL OF NATURAL PRODUCTS, 2017, 80 (10) :2734-2740

[2] Thiourea as a Template for Photodimerization of Azastilbenes [J].

Bhogala, Balakrishna R. ;

Captain, Burjor ;

Parthasarathy, Anand ;

Ramamurthy, V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) :13434-13442

[3] Template effects and supramolecular control of photoreactions in solution [J].

Bibal, Brigitte ;

Mongin, Cedric ;

Bassani, Dario M. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (12) :4179-4198

[4] Crystal engineering of topochemical solid state reactions [J].

Biradha, Kumar ;

Santra, Ramkinkar .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (03) :950-967

[5] Template-controlled reactivity in the organic solid state by principles of coordination-driven self-assembly [J].

Bucar, Dejan-Kresimir ;

Papaefstathiou, Giannis S. ;

Hamilton, Tamara D. ;

Chu, Qianli L. ;

Georgiev, Ivan G. ;

MacGillivray, Leonard R. .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2007, (29) :4559-4568

[6] Metal-carbene unit: a universal tool towards high-efficient photochemical reaction in solution [J].

Cao, Chen ;

Lang, Jianping .

SCIENCE CHINA-CHEMISTRY, 2019, 62 (06) :655-656

[7] Halogen bonding and π•••π stacking control reactivity in the solid state [J].

Caronna, T ;

Liantonio, R ;

Logothetis, TA ;

Metrangolo, P ;

Pilati, T ;

Resnati, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (14) :4500-4501

[8] A single-crystal-to-single-crystal transformation mediated by argentophilic forces converts a finite metal complex into an infinite coordination network [J].

Chu, QL ;

Swenson, DC ;

MacGillivray, LR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) :3569-3572

[9] Naturally occurring bioactive Cyclobutane-containing (CBC) alkaloids in fungi, fungal endophytes, and plants [J].

Dembitsky, Valery M. .

PHYTOMEDICINE, 2014, 21 (12) :1559-1581

[10]

Frii T., 2004, ORG LETT, V6, P4647

← 1 2 3 4 5 6 7 →