Microwave effects in metal-catalyzed reactions

Mini-Reviews in Organic Chemistry

Volumn 8, Issue 3, 2011, Pages 334-340

  Tsukahara, Yasunori ^a   Douke, Toshihiko ^a   Yamauchi, Tomohisa ^a   Wada, Yuji ^a,b  

^a OSAKA UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Metal catalyst; Microwave effect

Indexed keywords

CATALYSIS; CATALYSTS;

CATALYZED REACTIONS; ECO-FRIENDLY; GREEN-CHEMISTRY; METAL CATALYST; METAL-CATALYZED; MICROWAVES EFFECTS; ORGANICS; SUZUKI-HECK REACTIONS; SUZUKI-MIYAURA REACTION;

SUSTAINABLE CHEMISTRY;

EID: 79959981731     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019311796197427     Document Type: Review

References (54)

1. Perreux, L.; Loupy, A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium, and mechanistic considerations. Tetrahedron, 2001, 57, 9199-9223.
2. Kappe, C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed., 2004, 43, 6250-6284.
3. de la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Microwaves in organic synthesis. Thermal and non-thermal microwave effects. Chem. Soc. Rev., 2005, 34, 164-178.
4. Bose, A. K.; Manhas, M. S.; Ganguly, S. N.; Sharma, A. H.; Banik, B. K. MORE chemistry for less pollution: Applications for process development. Synthesis, 2002, 11, 1578-1591.
5. Polshettiwar, V.; Varma, R. S. Green chemistry by nano-catalysis. Green Chem., 2010, 12, 743-754.
6. Diederich, F.; Stang, P. J. Eds. Metal-Catalyzed Cross-Coupling Reactions. Wiley-VCH: Weinheim, Germany, 1998.
7. Suzuki, A. Organoborates in new synthetic reactions. Acc. Chem. Res. 1982, 15, 178-184.
8. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
9. Cerezo, V.; Amblard, M.; Martinez, J.; Verdie, P.; Planas, M.; Feliu, L. Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling. Tetrahedron, 2008, 64, 10538-10545.
10. Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. Regioselective palladium crosscoupling of 2,4-dihalooxazoles: Convergent synthesis of trisoxazoles. J. Org. Chem., 2008, 73, 3303-3306.
11. Harrisson, P.; Morris, J.; Marder, T. B.; Steel, P. G. Microwave-accelerated iridium-catalyzed borylation of aromatic C-H bonds. Org. Lett., 2009, 11, 3586-3589.
12. Kabri, Y.; Gellis, A.; Vanelle, P. Synthesis of original 2-substituted 4-arylquinazolines by microwave-irradiated Suzuki-Miyaura cross-coupling reactions. Eur. J. Org. Chem. 2009, 4059-4066.
13. Leadbeater, N. E.; Marco, M. Transition-metal-free Suzuki-type coupling reactions. Angew. Chem. Int. Ed., 2003, 42, 1407-1409.
14. Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. A reassessment of the transition-metal free Suzuki-type coupling methodology. J. Org. Chem., 2005, 70, 161-168.
15. Arvela, R. K.; Leadbeater, N. E. Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating simultaneous cooling. Org. Lett., 2005, 11, 2101-2104.
16. Schmink, J. R.; Kormos, C. M.; Devine, W. G.; Leadbeater, N. E. Exploring the scope for scale-up of organic chemistry using a large batch microwave reactor. Org. Process Res. Dev., 2010, 14, 205-214.
17. Diederich, F., Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions. Wiley-VCH: Weinheim, Germany, 1998.
18. Heck, R. F.; Nolley, J. P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem., 1972, 37, 2320-2322.
19. Tian, J.; Maurer, K.; Tesfu, E.; Moeller, K. D. Building addressable libraries: The use of electrochemistry for spatially isolating a heck eeaction on a chip. J. Am. Chem. Soc., 2005, 127, 1392-1393.
20. Larhed, M.; Hallberg, A. Microwave-promoted palladium-catalyzed coupling reactions. J. Org. Chem., 1996, 61, 9582-9584.
21. Palmisano, G.; Bonrath, W.; Boffa, L.; Garella, D.; Barge, A.; Cravotto, G. Heck reactions with very low ligandless catalyst loads accelerated by microwaves or simultaneous microwaves/ultrasound irradiation. Adv. Synth. Catal. 2007, 349, 2338-2344.
22. Kormos, C. M.; Leadbeater, N. E. Preparation of nonsymmetrically substituted stilbenes in a one-pot two-step Heck strategy using ethene as a reagent. J. Org. Chem., 2008, 73, 3854-3858.
23. Yilmaz, U.; Sireci, N.; Deniz, S.; Kucukbay, H. Synthesis and microwaveassisted catalytic activity of novel bis-benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross-coupling reactions. Appl. Organometal. Chem. 2010, 24, 414-420.
24. Moro, A. V.; Cardoso, F. S. P.; Correia, C. R. D. Highly regio-and stereoselective Heck reaction of allylic esters with arenediazonium salts: Application to the synthesis of kavalactones. Org. Lett., 2009, 11, 3642-3645.
25. Niembro, S.; Shafir, A.; Vallribera, A.; Alibes, R. Palladium nanoparticles supported on an organic-inorganic fluorinated hybrid material. Application to microwave-based Heck reaction. Org. Lett., 2008, 10, 3215-3218.
26. Diederich, F.; Stang, P. J. Eds. Metal-Catalyzed Cross-Coupling Reactions: Wiley-VCH: Weinheim, Germany, 1998.
27. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett., 1975, 16, 4467-4470.
28. McGuinness, D S.; Cavell, K. J. Donor-functionalized heterocyclic carbene complexes of palladium(II): Efficient catalysts for C-C coupling reactions. Organometallics, 2000, 19, 741-748.
29. Erdelyi, M.; Gogoll, A. Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating. J. Org. Chem., 2001, 66, 4165-4169.
30. Kim, D.-S.; Ham, J. Preparation of potassium alkynylaryltrifluoroborates from haloaryltrifluoroborates via Sonogashira coupling reaction. Org. Lett., 2010, 12, 1092-1095.
31. Huang, H.; Liu, H.; Jiang, H.; Chen, K. Rapid and efficient Pd-catalyzed Sonogashira coupling of aryl chlorides. J. Org. Chem. 2008, 73, 6037-6040.
32. Mehta, V. P.; Sharma, A.; Van der Eycken, E. The first palladium-catalyzed desulfitative Sonogashira-type cross-coupling of (hetero)aryl thioethers with terminal alkynes. Org. Lett. 2008, 10, 1147-1150.
33. Shook, B. C.; Chakravarty, D.; Jackson, P. F. Microwave-assisted Sonogashira-type cross couplings of various heterocyclic methylthioethers. Tetrahedron Lett., 2009, 50, 1013-1015.
34. Carpita, A.; Ribecai, A. Convenient copper-and solvent-free Sonogashiratype alkynylation of aryl iodides and bromides using Pd EnCat™. Tetrahedron Lett. 2009, 50, 204-207.
35. Liebeskind, L. S.; Srogl, J. Thiol ester-boronic acid coupling. A mechanistically unprecedented and general ketone synthesis. J. Am. Chem. Soc. 2000, 122, 11260-11261.
36. Baxendale, I. R.; Ley, S. V.; Smith, C. D.; Tamborini, L.; Voica, A.-F. A bifurcated pathway to thiazoles and imidazoles using a modular flow microreactor. J. Comb. Chem. 2008, 10, 851-857.
37. Arshad, N.; Hashim, J.; Kappe, C. O. Palladium(0)-catalyzed, copper(I)-mediated coupling of cyclic thioamides with alkenylboronic acids, organostannanes, and siloxanes. J. Org. Chem. 2009, 74, 5118-5121.
38. Mehta, V. P.; Sharma, A.; Van Hecke, K.; Van Meervelt, L.; Van der Eycken, E. A novel and versatile entry to asymmetrically substituted pyrazines. J. Org. Chem. 2008, 73, 2382-2388.
39. Lengar, A.; Kappe, C. O. Tunable carbon-carbon and carbon-sulfur crosscoupling of boronic acids with 3,4-dihydropyrimidine-2-thiones. Org. Lett, 2004, 6, 771-774.
40. Singh, B. K.; Mehta, V. P.; Parmar, V. S.; Van der Eycken. Palladiumcatalyzed copper(I)-mediated cross-coupling of arylboronic acids and 2(1H)-pyrazinones facilitated by microwave irradiation with simultaneous cooling. Org. Biomol. Chem. 2007, 5, 2962-2965.
41. Yasuda, M.; Somyo, T.; Baba, A. Direct carbon-carbon bond formation from alcohols and active methylenes, alkoxyketones, or indoles catalyzed by indium trichloride. Angew. Chem. Int. Ed., 2006, 45, 793-796.
42. Rueping, M.; Nachtsheim, B. J.; Kuenkel, A. Efficient metal-catalyzed direct benzylation and allylic alkylation of 2,4-pentanediones. Org. Lett., 2007, 9, 825-828.
43. Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid brønsted acids. J. Org. Chem., 2007, 72, 6006-6015.
44. Babu, S. A.; Yasuda, M.; Tsukahara, Y.; Yamauchi, T.; Wada, Y.; Baba, A. Microwave-irradiated transition-metal catalysis: rapid and efficient dehydrative carbon-carbon coupling of alcohols with active methylenes. Synthesis, 2008, 11, 1717-1724.
45. Mathew, P.; Prasidha, M.; Asokan, C. V. Microwave assisted one-pot synthesis of pyrrolo[2,1-b]thiazol-6-ones from α-aroyl ketene-N, S-acetals. J. Heterocycl. Chem., 2010, 47, 430-435.
46. Jones, J. R.; Lockley, W. J. S.; Lu, S.-Y.; Thompson, S. P. Microwaveenhanced aromatic dehalogenation studies: a rapid deuterium-labelling procedure. Tetrahedron Lett., 2001, 42, 331-332.
47. Wada, Y.; Yin, H.; Yanagida, S. Environmental remediation using catalysis driven under electromagnetic irradiation. Catal. Surv. Jpn., 2002, 5, 127-138.
48. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. Microwaveinduced organic reaction enhancement chemistry. 2. Simplified techniques. J. Org. Chem., 1991, 56, 6968-6970.
49. Banik, B. K.; Barakat, K. J.; Wagle, D. R.; Manhas, M. S.; Bose, A. K. Microwave-assisted rapid and simplified hydrogenation. J. Org. Chem., 1999, 64, 5746-5753.
50. Tsukahara, Y.; Higashi, A.; Yamauchi, T.; Nakamura, T.; Yasuda, M.; Baba, A.; Wada, Y. In situ observation of nonequilibrium local heating as an origin of special effect of microwave on chemistry. J. Phys. Chem. C, 2010, 114, 8965-8970.
51. Conner, W. C.; Tompsett, G. A. How could and do microwaves influence chemistry at interfaces?. J. Phys. Chem. B, 2008, 112, 2110-2118.
52. Riva, E.; Gagliardi, S.; Mazzoni, C.; Passarella, D.; Rencurosi, A.; Vigo, D.; Martinelli, M. Efficient continuous flow synthesis of hydroxamic acids and suberoylanilide hydroxamic acid preparation. J. Org. Chem., 2009, 74, 3540-3543.
53. Dressen, M. H. C. L.; van de Kruijs, B. H. P.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Flow processing of microwave-assisted (Heterogeneous) organic reactions. Org. Process Res. Dev., 2010, 14, 351-361.
54. Leadbeater, N. E.; Barnard, T. M.; Stencel, L. M. Batch and continuous-flow preparation of biodiesel derived from butanol and facilitated by microwave heatin. Energy Fuels, 2008, 22, 2005-2008.