The use of microwave ovens for rapid organic synthesis

Gedye, Richard; Smith, Frank E.; Westaway, Kenneth Charles; Ali, Hayder Mohsin; Baldisera, Lorraine; Laberge, Lena; Rousell, John

doi:10.1016/s0040-4039(00)83996-9

Cited by 1,579 publications

(714 citation statements)

References 4 publications

Supporting

Mentioning

687

Contrasting

Unclassified

Order By: Relevance

“…Therefore, it is not surprising that efficient and rapid microwave-assisted protocols have been developed for their preparation. In 2002 Fürstner and Seidel outlined the synthesis of pinacol aryl boronates from aryl chlorides bearing electron-withdrawing groups and commercially available bis(pinacol)borane (3), using a palladium catalyst formed in situ from Pd(OAc) 2 and imidazolium chloride 5 (Scheme 6, X = Cl). [80] The very reactive Nheterocyclic carbene (NHC) ligand (6-12 mol %) allowed this transformation to proceed to completion within 10-20 minutes at 110 8C in THF by using microwave irradiation in sealed vessels.…”

Section: Suzuki Reactionsmentioning

confidence: 99%

“…[1] More than 2000 articles have been published in the area of microwaveassisted organic synthesis (MAOS) since the first reports on the use of microwave heating to accelerate organic chemical transformations by the groups of Gedye and Giguere/ Majetich in 1986. [2,3] The initial slow uptake of the technology in the late 1980s and early 1990s has been attributed to its lack of controllability and reproducibility, coupled with a general lack of understanding of the basics of microwave dielectric heating. The risks associated with the flammability of organic solvents in a microwave field and the lack of available systems for adequate temperature and pressure controls were major concerns.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Controlled Microwave Heating in Modern Organic Synthesis

2004

View full text Add to dashboard Cite

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 The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction.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.

show abstract

Section: Suzuki Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

View full text Add to dashboard Cite

show abstract

“…The use of microwave irradiation to accelerate chemical or enzymatic reactions has been extensively explored. The first demonstration of microwave-assisted organic synthesis was made independently in the research laboratories of Giguere [25] and Gedye [26]. Since then, microwave irradiation has been used to assist in various chemical reactions [27,28].…”

mentioning

confidence: 99%

Microwave-assisted acid hydrolysis of proteins combined with liquid chromatography MALDI MS/MS for protein identification

Zhong

Marcus

2005

J. Am. Soc. Mass Spectrom.

152

142

View full text Add to dashboard Cite

Simple and efficient digestion of proteins, particularly hydrophobic membrane proteins, is of significance for comprehensive proteome analysis using the bottom-up approach. We report a microwave-assisted acid hydrolysis (MAAH) method for rapid protein degradation for peptide mass mapping and tandem mass spectrometric analysis of peptides for protein identification. It uses 25% trifluoroacetic acid (TFA) aqueous solution to dissolve or suspend proteins, followed by microwave irradiation for 10 min. This detergent-free method generates peptide mixtures that can be directly analyzed by liquid chromatography (LC) matrix-assisted laser desorption ionization (MALDI) mass spectrometry (MS) without the need of extensive sample cleanup. LC-MALDI MS/MS analysis of the hydrolysate from 5 g of a model transmembrane protein, bacteriorhodopsin, resulted in almost complete sequence coverage by the peptides detected, including the identification of two posttranslational modification sites. Cleavage of peptide bonds inside all seven transmembrane domains took place, generating peptides of sizes amenable to MS/MS to determine possible sequence errors or modifications within these domains. Cleavage specificity, such as glycine residue cleavage, was observed. Terminal peptides were found to be present in relatively high abundance in the hydrolysate, particularly when low concentrations of proteins were used for MAAH. It was shown that these peptides could still be detected from MAAH of bacteriorhodopsin at a protein concentration of 1 ng/ l or 37 fmol/ l. To evaluate the general applicability of this method, it was applied to identify proteins from a membrane protein enriched fraction of cell lysates of human breast cancer cell line MCF7. With one-dimensional LC-MALDI MS/MS, a total of 119 proteins, including 41 membrane-associated or membrane proteins containing one to 12 transmembrane domains, were identified by MS/MS database searching based on matches of at least two peptides to a protein. (J Am Soc Mass Spectrom 2005, 16, 471-481)

show abstract

“…Two seminal papers [8,9] appeared in 1986 that demonstrated that a variety of organic reactions could be completed in minutes instead of hours when conducted in sealed glass or Teflon vessels in domestic microwave ovens. A few explosions caused by the rapid rise of pressure in sealed systems were also reported.…”

Section: Microwave Technologymentioning

confidence: 99%

Microwave enhanced akabori reaction for peptide analysis

Bose

Ing

Lavlinskaia

et al. 2002

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

The Akabori reaction, devised in 1952 for the identification of C-terminus amino acids, involves the heating of a linear peptide in the presence of anhydrous hydrazine in a sealed tube for several hours. We report here a modified Akabori reaction that rapidly identifies the C-terminus amino acid in a polypeptide including its amino acid sequence information at both the C-terminus and the N-terminus. This modified methodology demonstrates the fundamentals of microwave chemistry applied to bioanalytical problems. In this modified process, hydrazinolysis has been accelerated by the application of microwave irradiation. In our reaction, the linear peptide and hydrazine solution, contained in a loosely covered conical flask, was exposed to a few minutes of irradiation using an unmodified domestic microwave oven. While the classical Akabori reaction required several hours, the microwave assisted reaction takes just minutes. If dimethyl sulfoxide is added to dilute the reaction mixture, the process is retarded enough to allow aliquots of the reaction mixture to be drawn every few minutes over a period of about an hour in order to study the progress of hydrazinolysis. Reaction products were monitored by mass spectrometry-primarily FAB-MS. In addition to providing sequence information, the microwave enhanced Akabori reaction quickly detects the presence of arginine (Arg) by converting each Arg to ornithine (Orn). Furthermore, certain amino acids, containing ␤-SH, CO 2 H, and CONH 2 groups in their side chain, are susceptible to modification by hydrazine, thereby, providing rapid confirmation of the presence of these amino acid residues. In these preliminary studies, the following oligopeptides were analyzed to demonstrate the effectiveness of our approach; the dipeptide (Trp-Phe), the tripeptide (Tyr-Gly-Gly), the tetrapeptide (Pro-Phe-Gly-Lys), the heptapeptide (Ala-Pro-Arg-Leu-ArgPhe-Tyr), and a N-terminal blocked tripeptide (N-acetyl-Met-Leu-Phe). (J Am Soc Mass Spectrom 2002, 13, 839 -850)

show abstract

The use of microwave ovens for rapid organic synthesis

Cited by 1,579 publications

References 4 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Microwave-assisted acid hydrolysis of proteins combined with liquid chromatography MALDI MS/MS for protein identification

Microwave enhanced akabori reaction for peptide analysis

Contact Info

Product

Resources

About