CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes

被引：16

作者：

Miyazaki, Yuta ^{[1
]}

Kahlfuss, Christophe ^{[2
]}

Ogawa, Ayumu ^{[1
]}

Matsumoto, Takashi ^{[3
]}

Wytko, Jennifer A. ^{[2
]}

Oohora, Koji ^{[1
]}

Hayashi, Takashi ^{[1
]}

Weiss, Jean ^{[2
]}

机构：

[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, 2-1 Yamadaoka, Suita, Osaka 5650871, Japan

[2] Univ Strasbourg, CNRS, UMR 7177, Inst Chim, 4 Rue Blaise Pascal, F-67000 Strasbourg, France

[3] Rigaku Corp, Applicat Labs, 3-9-12 Matsubara Cho, Akishima, Tokyo 1968666, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 55期

关键词：

active template; CuAAC; cycloaddition; porphyrinoid; rotaxanes; AZIDE-ALKYNE CYCLOADDITION; CLICK-CHEMISTRY; EXCELLENT YIELD; COPPER; ROTAXANES; COMPLEXES; OLIGOMERS; LIGANDS;

D O I：

10.1002/chem.201702553

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of a porphyrin rotaxane by dipolar cycloaddition takes advantage of the ditopic character of a phenanthroline-strapped porphyrin. The success of the click reaction was conditioned by the presence of both a coordinatively unsaturated metal in the porphyrin and a copper(I) bound to the phenanthroline, pointing at a new tandem active metal template mechanism.

引用

页码：13579 / 13582

页数：4

共 38 条

[1] [Anonymous], 2016, ROTAXANES ANGEW CHEM, DOI [10.1002/anie.20160664027600208, DOI 10.1002/ANIE.201606640]
[2] [Anonymous], ANGEW CHEM
[3] Catalytic "click" rotaxanes:: A substoichiometric metal-template pathway to mechanically interlocked architectures
Aucagne, V
Hänni, KD
Leigh, DA
Lusby, PJ
Walker, DB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) : 2186 - 2187
[4] Catalytic "Active-Metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the Cu(I)-catalyzed azide-alkyne 1,3-cycloaddition
Aucagne, Vincent
Berna, Jose
Crowley, James D.
Goldup, Stephen M.
Haenni, Kevin D.
Leigh, David A.
Lusby, Paul J.
Ronaldson, Vicki E.
Slawin, Alexandra M. Z.
Viterisi, Aurlien
Walker, D. Barney
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (39) : 11950 - 11963
[5] Synthesis of a Molecular Charm Bracelet via Click Cyclization and Olefin Metathesis Clipping
Clark, Paul G.
Guidry, Erin N.
Chan, Wing Yan
Steinmetz, Wayne E.
Grubbs, Robert H.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) : 3405 - 3412
[6] Nanorings with copper(II) and zinc(II) centers: forcing copper porphyrins to bind axial ligands in heterometallated oligomers
Cremers, Jonathan
Richert, Sabine
Kondratuk, Dmitry V.
Claridge, Tim D. W.
Timmel, Christiane R.
Anderson, Harry L.
[J]. CHEMICAL SCIENCE, 2016, 7 (12) : 6961 - 6968
[7] An Unusual Nickel-Copper-Mediated Alkyne Homocoupling Reaction for the Active-Template Synthesis of [2]Rotaxanes
Crowley, James D.
Goldup, Stephen M.
Gowans, Nicholas D.
Leigh, David A.
Ronaldson, Vicki E.
Slawin, Alexandra M. Z.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 6243 - 6248
[8] Side selection of the fifth coordinate with a single strapped zinc(II) porphyrin host: Full characterization of two imidazole complexes
Froidevaux, J
Ochsenbein, P
Bonin, M
Schenk, K
Maltese, P
Gisselbrecht, JP
Weiss, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12362 - 12363
[9] NEW TRIARYLMETHYL DERIVATIVES - BLOCK GROUPS - FOR ROTAXANES AND POLYROTAXANES
GIBSON, HW
LEE, SH
ENGEN, PT
LECAVALIER, P
SZE, J
SHEN, YX
BHEDA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (14) : 3748 - 3756
[10] PHENANTHROLINE-ASSISTED METALATION OF A PORPHYRIN - COPPER AND SILVER MIXED-VALENCE HOMODINUCLEAR COMPLEXES
GIRAUDEAU, A
GISSELBRECHT, JP
GROSS, M
WEISS, J
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (13) : 1103 - 1105

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