Olefin Metathesis Reaction in Water and in Air Improved by Supramolecular Additives

被引：12

作者：

Tomasek, Jasmine ^{[1
]}

Sessler, Miriam ^{[1
]}

Groeger, Harald ^{[2
]}

Schatz, Juergen ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Dept Chem & Pharm, Organ Chem 1, D-91054 Erlangen, Germany

[2] Univ Bielefeld, Fac Chem, D-33615 Bielefeld, Germany

来源：

MOLECULES | 2015年 / 20卷 / 10期

关键词：

aqueous metathesis; supramolecular chemistry; C-C coupling; AQUEOUS-SOLUTION; CALIXARENES; COMPLEXES; NMR; CYCLODEXTRINS; ASSOCIATION; CONSTANTS; PHOSPHINE; CATALYSTS; MEDIA;

D O I：

10.3390/molecules201019130

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A range of water-immiscible commercially available Grubbs-type precatalysts can be used in ring-closing olefin metathesis reaction in high yields. The synthetic transformation is possible in pure water under ambient conditions. Sulfocalixarenes can help to boost the reactivity of the metathesis reaction by catalyst activation, improved mass transfer, and solubility of reactants in the aqueous reaction media. Additionally, the use of supramolecular additives allows lower catalyst loadings, but still high activity in pure water under aerobic conditions.

引用

页码：19130 / 19141

页数：12

共 33 条

[1] GIAO-DFT calculated and experimentally derived complexation-induced chemical shifts of calix[4]arene-solvent inclusion complexes
Backes, AC
Schatz, J
Siehl, HU
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2002, (03): : 484 - 488
[2] Olefin metathesis in homogenous aqueous media catalyzed by conventional ruthenium catalysts
Binder, Joseph B.
Blank, Jacqueline J.
Raines, Ronald T.
[J]. ORGANIC LETTERS, 2007, 9 (23) : 4885 - 4888
[3] Olefin metathesis for chemical biology
Binder, Joseph B.
Raines, Ronald T.
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2008, 12 (06) : 767 - 773
[4] Supramolecular trapping of phosphanes by cyclodextrins: A general approach to generate phosphane coordinatively unsaturated organometallic complexes
Binkowski-Machut, C
Canipelle, M
Bricout, H
Tilloy, S
Hapiot, F
Monflier, E
[J]. EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2006, 8 (08) : 1611 - 1619
[5] Receptors for organochlorine pesticides based on calixarenes
Bocchinfuso, Gianfranco
Mazzuca, Claudia
Saracini, Claudio
Venanzi, Mariano
Micheli, Laura
Palleschi, Giuseppe
Palleschi, Antonio
[J]. MICROCHIMICA ACTA, 2008, 163 (3-4) : 195 - 202
[6] Metathesis in Pure Water Mediated by Supramolecular Additives
Brendgen, Thomas
Fahlbusch, Tilmann
Frank, Markus
Schuehle, Daniel T.
Sessler, Miriam
Schatz, Juergen
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) : 303 - 307
[7] Aqueous Olefin Metathesis
Burtscher, Daniel
Grela, Karol
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) : 442 - 454
[8] Alkyne-Enol Ether Cross-Metathesis in the Presence of CuSO4: Direct Formation of 3-Substituted Crotonaldehydes in Aqueous Medium
Castagnolo, Daniele
Botta, Lorenzo
Botta, Maurizio
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08) : 3172 - 3174
[9] Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry
Clavier, Herve
Nolan, Steven P.
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (06) : 841 - 861
[10] Practical olefin metathesis in protic media under an air atmosphere
Connon, SJ
Rivard, M
Zaja, M
Blechert, S
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (05) : 572 - 575

← 1 2 3 4 →