Microwave-Assisted Synthesis Utilizing Supported Reagents:  A Rapid and Efficient Acylation Procedure

Sauer, Daryl R.; Kalvin, and Douglas; Phelan, Kathleen

doi:10.1021/ol0358915

Cited by 55 publications

(35 citation statements)

References 12 publications

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“…Examples of resin-bound reactions: synthesis of 1,3,4-oxadiazoles using Burgess reagent, [249] Wittig reactions with triarylphosphanes, [250] catalytic transfer reaction involving formate, [251] O-alkylation with O-alkyl isoureas, [252] and formation of amide bonds with carbodiimide. [253] HOBt = 1-hydroxybenzotriazole.…”

Section: Microwave Chemistrymentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Microwave Chemistrymentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“… Anwendungsbeispiele für polystyrolgebundene Reagentien: Synthese von 1,3,4‐Oxadiazolen mit einem Burgess‐Reagens,249 Wittig‐Reaktionen mit Triarylphosphanen,250 katalytischer Wasserstofftransfer mit Formiat,251 O‐Alkylierung mit O‐Alkylisoharnstoffen252 und Bildung von Amidbindungen mit Carbodiimid 253. HOBt=1‐Hydroxybenzotriazol.…”

Section: Literaturüberblickunclassified

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

Kappe

2004

Angewandte Chemie

247

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Die offene Flamme konnte erst gezielt als Heizquelle für Reaktionsgefäße in der Synthesechemie verwendet werden, nachdem Robert Bunsen 1855 den nach ihm benannten Brenner erfunden hatte. Der Bunsen‐Brenner wurde später durch den Heizpilz, das Ölbad und die Heizplatte als Wärmequellen für chemische Reaktionen abgelöst. In den vergangenen Jahren ist das Erhitzen und Beschleunigen chemischer Reaktionen durch Mikrowellenenergie populär geworden. Diese Heiztechnik hat sich von einer Laborkuriosität zu einer etablierten Methode entwickelt, die an Universitäten und in der Industrie stark genutzt wird. Die effiziente Verringerung der Reaktionszeiten (von Tagen und Stunden auf Minuten und Sekunden) ist nur einer der vielen Vorteile des schnellen Erhitzens mit Mikrowellen (“microwave flash heating”). Dieser Aufsatz gibt einen Überblick über neuere Anwendungen des kontrollierten Mikrowellenerhitzens in der modernen organischen Synthese und diskutiert einige grundlegende Vorgänge.

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“…Microwave-assisted reactions are believed to facilitate polarization of the substrates thereby promoting the reactions [24][25][26]. Microwave-assisted reactions have become increasingly important in tetrapyrolic compounds synthesis due to advantages such as: significant reduction in reaction times, side reactions, increased yields, ease of purification, and minimization of the amount of solvent used [27,28].…”

mentioning

confidence: 99%

Microwave-assisted Synthesis of Unsymmetrical Tetrapyrrolic Compounds

Socoteanu¹,

Boscencu²,

Nacea³

et al. 2008

Rev. Chim.

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Unsymmetrical porphyrin, 5-(3-hydroxyphenyl)-10,15,20-tris-(4-carboxymethylphenyl)-21,23-H-porphine (TCMPOHM) and also the parent symmetrical compound 5,10,15,20-meso-tetrakis-(4-carboxymethylphenyl)-21,23H porphine (TCMP) were synthesized with superior yields using microwave irradiation. Structures were confirmed by 1H-NMR, 13C-NMR, UV-Vis and FTIR spectroscopy. Various NMR experimental approaches (including 13C-NMR, DEPT, COSY, HMBC and HMQC) were used to completely elucidate some interesting aspects concerning the structure of the new porphyrin compounds.

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Microwave-Assisted Synthesis Utilizing Supported Reagents: A Rapid and Efficient Acylation Procedure

Abstract: [reaction: see text] The application of microwave heating to a polymer-assisted solution-phase (PASP) synthesis technique has been utilized to develop a rapid and efficient protocol for the solution-phase synthesis of amides from either amine or carboxylic acid cores.

Cited by 55 publications

References 12 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Kontrolliertes Erhitzen mit Mikrowellen in der modernen organischen Synthese

Microwave-assisted Synthesis of Unsymmetrical Tetrapyrrolic Compounds

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