Controlled Microwave Heating in Modern Organic Synthesis: Highlights from the 2004-2008 Literature

Overview

Journal Mol Divers

Date 2009 Apr 22

PMID 19381851

Citations 45

Authors

C Oliver Kappe

Doris Dallinger

Affiliations

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Abstract

Direct and rapid heating by microwave irradiation in combination with sealed vessel processing in many cases enables reactions to be carried out in a fraction of the time generally required using conventional conditions. This makes microwave chemistry an ideal tool for rapid reaction scouting and optimization of conditions, allowing very rapid progress through hypotheses-experiment-results iterations. The speed at which multiple variations of reaction conditions can be performed allows a morning discussion of "What should we try?" to become an after-lunch discussion of "What were the results?" Not surprisingly, therefore, many scientists both in academia and industry have turned to microwave synthesis as a front-line methodology for their projects. In this review, more than 220 published examples of microwave-assisted synthetic organic transformations from the 2004 to 2008 literature are discussed. An additional ca. 500 reaction schemes are presented in the Electronic Supplementary Material, providing the reader with an overall number of ca. 930 references in this fast-moving and exciting field.

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References

Kaleta Z, Tarkanyi G, Gomory A, Kalman F, Nagy T, Soos T . Synthesis and application of a fluorous Lawesson's reagent: convenient chromatography-free product purification. Org Lett. 2006; 8(6):1093-5. DOI: 10.1021/ol0529849. View

Lin M, Sun C . Microwave-assisted and traceless synthesis of imidazoquinoxalinones. J Comb Chem. 2006; 8(4):455-8. DOI: 10.1021/cc060051d. View

Strauss C . Microwave-assisted reactions in organic synthesis-are there any nonthermal microwave effects? Response to the highlight by N. Kuhnert. Angew Chem Int Ed Engl. 2002; 41(19):3589-91, 3513. DOI: 10.1002/1521-3773(20021004)41:19<3589::AID-ANIE3589>3.0.CO;2-Q. View

Sherman E, Fuller P, Kasi D, Chemler S . Pyrrolidine and piperidine formation via copper(II) carboxylate-promoted intramolecular carboamination of unactivated olefins: diastereoselectivity and mechanism. J Org Chem. 2007; 72(10):3896-905. PMC: 2590667. DOI: 10.1021/jo070321u. View

Baker B, Boskovic Z, Lipshutz B . (BDP)CuH: a "hot" Stryker's reagent for use in achiral conjugate reductions. Org Lett. 2007; 10(2):289-92. DOI: 10.1021/ol702689v. View

Bacsa B, Horvati K, Bosze S, Andreae F, Kappe C . Solid-phase synthesis of difficult peptide sequences at elevated temperatures: a critical comparison of microwave and conventional heating technologies. J Org Chem. 2008; 73(19):7532-42. DOI: 10.1021/jo8013897. View

Braga A, Paixao M, Westermann B, Schneider P, Wessjohann L . Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts. J Org Chem. 2008; 73(7):2879-82. DOI: 10.1021/jo702413n. View

Campeau L, Schipper D, Fagnou K . Site-selective sp2 and benzylic sp3 palladium-catalyzed direct arylation. J Am Chem Soc. 2008; 130(11):3266-7. DOI: 10.1021/ja710451s. View

Kesavan S, Panek J, Porco Jr J . Preparation of alkylidene indane and related scaffolds and their further elaboration to novel chemotypes. Org Lett. 2007; 9(25):5203-6. DOI: 10.1021/ol7023778. View

10.

Christoforou I, Koutentis P . New regiospecific isothiazole C-C coupling chemistry. Org Biomol Chem. 2006; 4(19):3681-93. DOI: 10.1039/b607442a. View

11.

Chang W, Kulkarni M, Sun C . Traceless and stereoselective synthesis of tetrahydro-beta-carbolinethiohydantoins by microwave irradiation. J Comb Chem. 2006; 8(2):141-4. DOI: 10.1021/cc050098j. View

12.

Kuhnert N . Microwave-assisted reactions in organic synthesis--are there any nonthermal microwave effects?. Angew Chem Int Ed Engl. 2009; 41(11):1863-6. DOI: 10.1002/1521-3773(20020603)41:11<1863::aid-anie1863>3.0.co;2-l. View

13.

Nie A, Wang J, Huang Z . Microwave-assisted solution-phase parallel synthesis of 2,4,6-trisubstituted pyrimidines. J Comb Chem. 2006; 8(5):646-8. DOI: 10.1021/cc060053y. View

14.

Manbeck G, Lipman A, Stockland Jr R, Freidl A, Hasler A, Stone J . Organosoluble copper clusters as precatalysts for carbon-heteroelement bond-forming reactions: microwave and conventional heating. J Org Chem. 2004; 70(1):244-50. DOI: 10.1021/jo048761y. View

15.

Rudolph A, Rackelmann N, Turcotte-Savard M, Lautens M . Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles. J Org Chem. 2008; 74(1):289-97. DOI: 10.1021/jo802180h. View

16.

Saaby S, Baxendale I, Ley S . Non-metal-catalysed intramolecular alkyne cyclotrimerization reactions promoted by focussed microwave heating in batch and flow modes. Org Biomol Chem. 2005; 3(18):3365-8. DOI: 10.1039/b509540a. View

17.

Gachkova N, Cassel J, Leue S, Kann N . The solid-phase Nicholas reaction: scope and limitations. J Comb Chem. 2005; 7(3):449-57. DOI: 10.1021/cc049835m. View

18.

Li J, Grennberg H . Microwave-assisted covalent sidewall functionalization of multiwalled carbon nanotubes. Chemistry. 2006; 12(14):3869-75. DOI: 10.1002/chem.200501314. View

19.

Palmer A, Grobbel B, Brehm C, Zimmermann P, Buhr W, Feth M . Preparation of tetrahydroimidazo[2,1-a]isoquinolines and their use as inhibitors of gastric acid secretion. Bioorg Med Chem. 2007; 15(24):7647-60. DOI: 10.1016/j.bmc.2007.08.065. View

20.

Mariampillai B, Alliot J, Li M, Lautens M . A convergent synthesis of polysubstituted aromatic nitriles via palladium-catalyzed C-H functionalization. J Am Chem Soc. 2007; 129(49):15372-9. DOI: 10.1021/ja075599i. View