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.
📌 3 Key Takeaways
🎯
Objective & Hypothesis:A highly effective, easy to handle and environmentally benign process for a palladium mediated Heck reaction was developed.
📊
Key Findings & Data:A highly effective, easy to handle and environmentally benign process for a palladium mediated Heck reaction was developed.
💡
Conclusion & Impact: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.
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.
Özet
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.
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).
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).