Application of commercial microwave ovens to organic synthesis.

Giguere, R. J.; Bray, Terry; Duncan, Scott M.; Majetich, George

doi:10.1016/s0040-4039(00)85103-5

Cited by 1,099 publications

(457 citation statements)

References 7 publications

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“…[10] Scheme 1 shows a recent example of a standard Heck reaction involving aryl bromides 1 and acrylic acid to furnish the corresponding cinnamic acids 2. [42] Optimization of the reaction conditions under small-scale (2 mmol) single-mode microwave conditions led to a protocol that employed MeCN as the solvent, 1 mol % Pd(OAc) 2 /P(o-tolyl) 3 as the catalyst system, and triethylamine as the base. The reaction time was 15 minutes at a reaction temperature of 180 8C.…”

Section: Heck Reactionsmentioning

confidence: 99%

“…Therefore, safety problems arising from overpressurization of heated sealed reaction vessels can be minimized. [45,46] In the Heck reactions shown in Scheme 2, 4 mol % of PdCl 2 /P(o-tolyl) 3 was used. Full conversions were achieved within 5 (X = I) and 20 minutes (X = Br).…”

Section: Heck Reactionsmentioning

confidence: 99%

“…[61] For the Heck coupling shown in Scheme 3, the air-stable but highly reactive [(tBu) 3 PH]BF 4 phosphonium salt described by Netherton and Fu [62] was employed as a ligand precursor using the palladacycle [63] developed by Herrmann et al as the palladium precatalyst. Depending on the reactivity of the aryl chloride, 1.5-10 mol % of Pd catalyst (3-20 % of ligand), 1.5 equivalents of Cy 2 NMe as a base, and 1.0 equivalent of [bmim]PF 6 in dioxane were irradiated at 180 8C under sealedvessel conditions (no inert gas atmosphere) with the aryl chloride and butyl acrylate for 30-60 min.…”

Section: Microwave Chemistrymentioning

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%

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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: Heck Reactionsmentioning

confidence: 99%

Section: Heck Reactionsmentioning

confidence: 99%

Section: Microwave Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…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.

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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)

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Synthesis of cyclic esters of N-toluenesulfonyl ?-aminophosphonic acid

Dai

Chen

1998

Heteroatom Chem.

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Application of commercial microwave ovens to organic synthesis.

Cited by 1,099 publications

References 7 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Microwave enhanced akabori reaction for peptide analysis

Synthesis of cyclic esters of N-toluenesulfonyl ?-aminophosphonic acid

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