Reusable Polymer-Supported Terpyridine Palladium Complex for Suzuki-Miyaura, Mizoroki-Heck, Sonogashira, and Tsuji-Trost Reaction in Water

Polymers

Volumn 3, Issue 1, 2011, Pages 621-639

  Suzuka, Toshimasa ^a   Kimura, Kosuke ^a   Nagamine, Takuya ^a  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

Cross coupling; Palladium; Polymer supported synthesis; Terpyridine

Indexed keywords

CHEMICAL REACTIONS; PALLADIUM COMPOUNDS; TRANSITION METALS;

AEROBIC CONDITION; CROSS-COUPLINGS; PALLADIUM COMPLEXES; POLYMER SUPPORTED SYNTHESIS; POLYMER-SUPPORTED; REACTIONS IN WATER; SUZUKI-MIYAURA; TERPYRIDINES; TRANSITION METAL CATALYSTS; TSUJI-TROST REACTION;

CATALYST ACTIVITY;

EID: 80255138997     PISSN: None     EISSN: 20734360     Source Type: Journal    
DOI: 10.3390/polym3010621     Document Type: Article

References (26)

1. Trost, B.M. The atom economy-A search for synthetic efficiency. Science 1991, 254, 1471-1477.
2. Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Synthesis; Wiley: New York, NY, USA, 1995.
3. Yin, L.; Liebscher, J. Carbon-carbon coupling reactions catalyzed heterogeneous palladium catalysts. Chem. Rev. 2007, 107, 133-173.
4. Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, NY, USA, 2004.
5. Heck, R.F. Palladium Reagents in Organic Synthesis; Academic: London, UK, 1985.
6. Tsuji, J.; Takahashi, H.; Morikawa, M. Organic synthesis by means of noble metal compounds XVII. Reaction of π-allylpalladium chloride with nucleophiles. Tetrahedron Lett. 1965, 6, 4387-4388.
7. Trost, B.M.; Fullerton, T.J. New synthetic reactions allylic alkylation. J. Am. Chem. Soc. 1973, 95, 292-294.
8. Mizoroki, T.; Mori, K.; Ozaki, A. Arylation of olefin with aryl iodine catalyzed by palladium. Bull. Chem. Soc. Jpn. 1971, 44, 581-581.
9. Heck, R.F.; Nolly, J.P. Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides. J. Org. Chem. 1972, 37, 2320-2322.
10. Miyaura, N.; Yanagi. T.; Suzuki, A. The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presence of bases. Synth. Commun. 1981, 11, 513-519.
11. Sonogashira, K.; Tohda, Y.; Hagihara, N. Convenient synthesis of acetylenes. Catalytic substitutions of acetylenic hydrogen with bromo alkenes, iodo arenes and bromopyridines. Tetrahedron Lett. 1975, 16, 4467-4470.
12. Beletskaya, I.P.; Cheprakov, A.V. The Heck reaction as a sharpening stone of palladium catalysis. Chem. Rev. 2000, 100, 3009-3066.
13. Chinchilla, R.; Nájera, C. The Sonogashira reaction: A booming methodology in synthetic organic chemistry. Chem. Rev. 2007, 107, 874-922.
14. Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 1995, 95, 2457-2483.
15. Trost, B.M.; Crawley, M.L. Asymmetric transition-metal-catalyzed allylic alkylations: Application in total synthesis. Chem. Rev. 2003, 103, 2921-2944.
16. Alonso, F.; Beletskaya, I.P.; Yus, M. Non-conventional methodologies for transition-metal catalyzed carbon-carbon coupling: A critical overview. Tetrahedron 2005, 61, 11771-11835.
17. Yin, L.; Liebscher, J. Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts. Chem. Rev. 2007, 107, 133-173.
18. For a review, see Sheldon, R.A.; I. Arends, U. Hanefeld, Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
19. For a review, see Ding, K.; Uozumi, Y. Handbook of Asymmetric Heterogeneous Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
20. Kann, K. Recent applications of polymer supported organometallic catalysts in organic synthesis. Molecules 2010, 15, 6306-6331.
21. Suzuka, T.; Ooshiro, K.; Kina, K. Reusable polymer-supported terpyridine copper complex for [3 + 2] Huisgen cycloaddition in water. Heterocycles 2010, 81, 601-610.
22. Suzuka, T.; Nagamine, T.; Ogihara, K.; Higa, M. Suzuki-Miyaura cross-coupling reaction in water with polymer-supported terpyridine palladium complex under aerobic conditions. Catal. Lett. 2010, 139, 85-89.
23. For a review of terpyridine-metal complexes, see Eryazici, I.; Moorefield, N.; Newkome, R. Square planar Pd(II), Pt(II), and Au(III) terpyridine complexes: Their synthesis, physical properties, supra-molecular constructs, and biomedical activities. Chem. Rev. 2008, 108, 1834-1895 and references therein.
24. For an example of immobilization of organometallic catalyst onto the solid-support through ionic bonds, see Uthaiwan, S.; Jin, B.Y.; Se, L.B.; Yoon, C.D. Ionic polymer supported copper(I): A reusable catalyst for Huisgen’s 1,3-diopar cycloaddition. Synlett 2008, 40, 2326-2330.
25. 3 in supported aqueous-phase. Is it really aqueous? Catal. Lett. 1990, 6, 43-48.
26. 2 resin at 100 °C for 6 h to give the biphenyl in 33% yield. ICP-AES analysis of the filtrate showed that the Pd content was 2.2 ppm.