Benzimidazolylidene Carbene Ligated Palladium Catalysis of the Heck Reaction in Aqueous Media
A highly effective, easy to handle and environmentally benign process for a palladium mediated Heck reaction was developed. The in situ prepared 3-component system, Pd(OAc)2 / 1,3-dialkylbenzimidazolium chlorides (LHX = 1a-g) and Cs2CO3, catalyzes quantitatively the Heck coupling of aryl bromides under mild conditions in aqueous media.
Benzimidazolylidene Carbene Ligated Palladium Catalysis of the Heck Reaction in Aqueous Media
A highly effective, easy to handle and environmentally benign process for a palladium mediated Heck reaction was developed. The in situ prepared 3-component system, Pd(OAc)2 / 1,3-dialkylbenzimidazolium chlorides (LHX = 1a-g) and Cs2CO3, catalyzes quantitatively the Heck coupling of aryl bromides under mild conditions in aqueous media.
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- R.F. Heck, Acc. Chem. Res. 12, 146-151 (1979).
- R.F. Heck, ”Comprehensive Organic Synthesis”, Vol . 4, eds. B.M. Trost and I. Fl emming, Chap. 4.3., Pergamon: New York, 1991.
- S. Brase and A. Meijere, ”In Metal Catalyzed Cross Coupling Reactions”, eds. F. Dienderich and P.J. Stang, Ch. 3, Wiley: New York, 1998.
- B. Cornills and W.A. Herrmann, ”Applied Homogenous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Two Volumes”, VCH Weinheim, 1996.
- I.P. Beletskaya and A.V. Cheprakov, Cem. Rev. 100, 3009-3066 (2000).
- S.J. Danishefsky, J.J. Masters, J.T. Link, L.B. Snyder, T.V. Magee, D.K. Jung, R.C.A. Isaac, W.G. Bornmann, C.A. Alaimo, C.A. Coburn and M.J. Di Grani, J. Am. Chem. Soc. 118, 2843-2859 (1996).
- S.C. Stinson, Chem. Eng. News. 77, 63-64 (1999).
- A.F. Littke and G.C. Fu, J. Am. Chem. Soc. 123, 6989-7000 (2001).
- J.P. Stambuli, S.R. Stauffer, K.H. Shaughnessy and J.F. Hartwig, J. Am. Chem. Soc. 123, 2677-2678 (2001).
- M.R. Netherton and G.C. Fu, Org. Lett. 3, 4295-4298 (2001).
- M. Ohff, A. Ohff, M.E. van der Boom and D. Milstein, J. Am. Chem. Soc. 119, 11687-11688 (1997).
- D.A. Albisson, R.B. Bedford and P.N. Scully, Tetrahedron Lett. 39, 9793-9796 (1998).
- M. Ohff, A. Ohff and D. Milstein, Chem. Commun. 357-358 (1999).
- S. Lyer and C. Ramesh, Tetrahedron Lett. 41, 8981-8984 (2000).
- W.A. Herrmann, T. Weskamp and V.P.W. B¨ohm, Adv. Organomet. Chem. 48, 1-69 (2001).
- J. Huang, H.J. Schanz, E.D. Stevens and S.P. Nolan, Organometallics 18, 2370-2375 (1999).
- J. Schwarz, V.P.W. B¨ohm, M.G. Gardiner, M. Grosche, W.A. Herrmann, W. Hieringer and G. Raudaschl- Sieber, Chem. Eur. J. 6, 1773-1780 (2000).
- C. Yang and S.P. Nolan, Synlett 10, 1539-1542 (2001).
- D. Bourissou, O. Guerret, F.P. Gabbai, and G. Bertrand, Chem. Rev. 100, 39-92 (2000).
- W.A. Herrmann and C. K¨ocher, Angew. Chem., Int. Ed. Engl. 36, 2162-2187 (1997).
- T.Y. Zhang and H. Zhang, Tetrahedron Lett. 43, 193-195 (2002).
- S. Lee and J.F. Hartwig, J. Org. Chem. 66, 3402-3415 (2001).
- J. Cheng, and M.L. Trudell, Org. Lett. 3, 1371-1374 (2001).
- A. F¨urstner and A. Leitner, Synlett 2, 290-292 (2001).
- L.R. Titcomb, S. Caddick, F.G.N. Cloke, D.J. Wilson and D. McKerrrecher, Chem. Commun. 1388-1389 (2001).
- S.R. Stauffer, S. Lee, J.P. Stambuli, S.I. Hauck and J.F. Hartwig, Org. Lett. 2, 1423-1426 (2000).
- C. Yang, H.M. Lee and S.P. Nolan, Org. Lett. 3, 1511-1514 (2001).
- D.S. McGuinness, K.J. Cavell, B.W. Skelton and A.H. White, Organometallics 18, 1596-1605 (1999).
- D.S. McGuinness, M.J. Green, K.J. Cavell, B.W. Skelton and A.H. White, J. Organomet. Chem. 565, 178 (1998).
- E. Peris, J.A. Loch, J. Mata and R.H. Crabtree, Chem. Commun. 201-202 (2001).
- C. Li and T.H. Chan, ”Organic Reactions in Aqueous Media”, Wiley, New York, 1997.
- J.-P. Genet and M. Savignac, J. Organomet. Chem. 576, 305-317 (1999).
- H. Sakurai, T. Sukuda and T. Hirao, J. Org. Chem. 67, 2721-2722 (2002).
- S. Parisot, R. Kol odziuk, C.G. Henry, A. Iourtchenko and D. Sinou, Tetrahedron Lett. 43, 7397-7400 (2002).
- L. Botella and C. Najera, Angew. Chem. Int. Ed. Eng. 41,179-181 (2002). D. Sch¨ onfelder, O. Nuyken and R.J. Weberskirch, J. Organomet. Chem. 690, 4648-4655 (2005).
- I. ¨Ozdemir, S. Demir, S. Ya¸sar and B. C¸ etinkaya, Appl. Organomet. Chem. 19, 55-58 (2005).
- I. ¨Ozdemir, S. Demir and B. C¸ etinkaya, Tetrahedron 61, 9791-9798 (2005).
- I. ¨Ozdemir, N. G¨urb¨uz, Y. G¨ok, E. C¸ etinkaya and B. C¸ etinkaya, Synlett 15, 2394-2396 (2005).
- I. ¨Ozdemir, Y. G¨ok, N. G¨urb¨uz, S. Ya¸sar, E. C¸ etinkaya and B. C¸ etinkaya, Polish J. Chem. 78, 2141-2147 (2004).
- I. ¨Ozdemir, Y. G¨ok, N. G¨urb¨uz, E. C¸ etinkaya and B. C¸ etinkaya, Synt. Commun. 34, 4135-4144 (2004).
- I. ¨Ozdemir, N. G¨urb¨uz, T. Se¸ckin and B. C¸ etinkaya, Appl. Organomet. Chem. 19, 633-638 (20005).
- I. ¨Ozdemir, Y. G¨ok, N. G¨urb¨uz, E. C¸ etinkaya and B. C¸ etinkaya, Heteroatom. Chem. 15, 419-423 (2004).
- O.V. Starikova, G.V. Dolgushin, L.I. Larina, P.E. Ushakov, T.N. Komarova and V. A. Lopyrev, Russ. J. Org. Chem. 39, 1467-1470 (2003).
- ˙I. ¨Ozdemir, Y. G¨ok, N. G¨urb¨uz, E. C¸ etinkaya and B. C¸ etinkaya, J. Heterocyclic Chem. 42, 303-306 (2005).
- D. Semeril, C. Bruneau and P.H. Dixneuf, Adv. Synth. Catal. 344, 585-595 (2002).
- D. Semeril, M.D. Cleran, C. Bruneau and P.H. Dixneuf, Adv. Synth. Catal. 343, 184-187 (2001).
- R. Castarlenes, Alaoui-Abdallaoui, D. Semeril, B. Mernari, and P.H. Dixneuf, New. J. Chem. 27, 6-9 (2003).
- A.C. Grasa, G.A. Viciu, M.S. Lee, H.M. Yang and S.P. Nolan, J. Organomet. Chem. 653, 69-82 (2002).
- C. Zhang and M.L. Trudell, Tetrahedron Lett. 41, 595-598 (2000).
- V. Farina, Adv. Synth. Catal. 346, 1553-1582 (2004).
- A.F. Littke and G.C. Fu, Angew. Chem. Int. Ed. 41, 4176-4211 (2002).
- J.A. Loch, M. Albrecht, E. Peris, J. Mata, J.W. Faller and R.H. Crabtree, Organometallics 21, 700-706 (2002).
- E. Peris and R.H. Crabtree, Coord. Chem. Rev. 248, 2239-2246 (2004).
- B. C¸ etinkaya, ˙I. ¨Ozdemir, C. Bruneau and P.H. Dixneuf, J. Mol. Catal A: 118, L1-L4 (1997).