Activation-Enabled Syntheses of Functionalized Pillar[5]arene Derivatives

被引：34

作者：

Han, Jie ^{[1
,2
]}

Hou, Xisen ^{[1
]}

Ke, Chenfeng ^{[1
]}

Zhang, Huacheng ^{[1
]}

Strutt, Nathan L. ^{[1
]}

Stern, Charlotte L. ^{[1
]}

Stoddart, J. Fraser ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

[2] Nankai Univ, Coll Chem, Tianjin 300071, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 13期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLING REACTIONS; CATALYZED SYNTHESIS; HOST; NANOPARTICLES; COMPLEXATION; CHLORIDES; REAGENTS; BROMIDES; HALIDES; FACILE;

D O I：

10.1021/acs.orglett.5b01418

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of regioselective di- and trifunctionalized pillar[5]arene derivatives have been synthesized by a deprotection-followed-by-activation strategy, and their constitutions have been established as a result of having access to their solid-state structures. De-O-methylation occurs in a stepwise manner at lower temperatures under kinetic control, affording the desired oligo-substituted pillar[5]arene derivatives. In addition, the regioisomers of these derivatives can be isolated by installing triflate groups on the free-hydroxyl groups.

引用

页码：3260 / 3263

页数：4

共 56 条

[1] More Chemistry in Small Spaces [J].

Ajami, Dariush ;

Rebek, Julius, Jr. .

ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (04) :990-999

[2] Mechanized Silica Nanoparticles: A New Frontier in Theranostic Nanomedicine [J].

Ambrogio, Michael W. ;

Thomas, Courtney R. ;

Zhao, Yan-Li ;

Zink, Jeffrey I. ;

Stoddartt, J. Fraser .

ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (10) :903-913

[3] A Facile and Efficient Preparation of Pillararenes and a Pillarquinone [J].

Cao, Derong ;

Kou, Yuhui ;

Liang, Jianquan ;

Chen, Zhizhao ;

Wang, Lingyun ;

Meier, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9721-9723

[4] A monophosphoryl copillar[5]arene: synthesis and host-guest complexation with alkanols [J].

Chen, Yu ;

He, Minqing ;

Li, Boqi ;

Wang, Lingyun ;

Meier, Herbert ;

Cao, Derong .

RSC ADVANCES, 2013, 3 (44) :21405-21408

[5] THE DESIGN OF MOLECULAR HOSTS, GUESTS, AND THEIR COMPLEXES (NOBEL LECTURE) [J].

CRAM, DJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (08) :1009-1020

[6] Review: A History of Cyclodextrins [J].

Crini, Gregorio .

CHEMICAL REVIEWS, 2014, 114 (21) :10940-10975

[7]

DIETRICH B, 1969, TETRAHEDRON LETT, P2885

[8] CUCURBITURIL [J].

FREEMAN, WA ;

MOCK, WL ;

SHIH, NY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (24) :7367-7368

[9] Low-Temperature Ag/Pd-Catalyzed Decarboxylative Cross-Coupling of Aryl Triflates with Aromatic Carboxylate Salts [J].

Goossen, Lukas J. ;

Lange, Paul P. ;

Rodriguez, Nuria ;

Linder, Christophe .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (13) :3906-3909

[10] Pillar[5]arene-based polymeric architectures constructed by orthogonal supramolecular interactions [J].

Guan, Yangfan ;

Ni, Mengfei ;

Hu, Xiaoyu ;

Xiao, Tangxin ;

Xiong, Shuhan ;

Lin, Chen ;

Wang, Leyong .

CHEMICAL COMMUNICATIONS, 2012, 48 (68) :8529-8531

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