European Journal of Chemistry

An N-heterocyclic carbene-palladium-η3-allyl chloride complex for the Suzuki-Miyaura coupling of aryl halides



Main Article Content

Noland William Broekemier
Noah Curtis Broekemier
Randall Thomas Short
Hector Palencia

Abstract

An unsymmetrical, well-defined N-heterocyclic carbene-palladium-η3-allyl chloride complex has been synthesized and used as an efficient catalyst for the Suzuki-Miyaura cross-coupling of aryl bromides and activated aryl chlorides. The catalyst provides moderate to high yields of cross-coupling products at 50 °C in 2 hours, using 1 mol % of the catalyst and isopropyl alcohol as solvent.


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Broekemier, N. W.; Broekemier, N. C.; Short, R. T.; Palencia, H. An N-Heterocyclic Carbene-Palladium-η3-Allyl Chloride Complex for the Suzuki-Miyaura Coupling of Aryl Halides. Eur. J. Chem. 2014, 5, 162-166.

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References

[1]. Suzuki, A. J. Organomet. Chem. 1999, 576(1-2), 147-168.
http://dx.doi.org/10.1016/S0022-328X(98)01055-9

[2]. Miyaura, N.; Suzuki Chem. Rev. 1995, 95, 2457-2483.
http://dx.doi.org/10.1021/cr00039a007

[3]. Suzuki, A. Overview of the Suzuki Protocol with B, in Handbook of organopalladium chemistry for organic synthesis, E. -I. Negishi, Editor. John Wiley & Sons, 2002, p. 249-262.
http://dx.doi.org/10.1002/0471212466.ch16

[4]. Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
http://dx.doi.org/10.1021/ja00001a054

[5]. Herrmann, W. A; Kocher, C. Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187.
http://dx.doi.org/10.1002/anie.199721621

[6]. Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676.
http://dx.doi.org/10.1021/cr900074m

[7]. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem. Int. Ed. 2007, 46, 2768-2813.
http://dx.doi.org/10.1002/anie.200601663

[8]. Viciu, M. S.; Navarro, O.; Germaneau, R. F.; Kelly III, R. A.; Sommer, W.; Marion, N.; Stevens, E. D.; Cavallo, L.; Nolan, S. P. Organometallics 2004, 23, 1629-1635.
http://dx.doi.org/10.1021/om034319e

[9]. Nasielski, J.; Hadei, N.; Achonduh, G.; Kantchev, A. B.; O'Brien, C. J.; Lough, A.; Organ, M. G. Chem. - Eur. J. 2010, 16, 10844-10853.
http://dx.doi.org/10.1002/chem.201000138

[10]. Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195-15201.
http://dx.doi.org/10.1021/ja045349r

[11]. Gstottmayr, C. W. K.; Bohm, V. P. W.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
http://dx.doi.org/10.1002/1521-3773(20020415)41:8<1363::AID-ANIE1363>3.0.CO;2-G

[12]. Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866-2873.
http://dx.doi.org/10.1021/om020178p

[13]. Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643.
http://dx.doi.org/10.1021/ja038177r

[14]. Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
http://dx.doi.org/10.1021/ja00074a085

[15]. Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
http://dx.doi.org/10.1021/ja9831352

[16]. Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 1998, 37, 2490-2493.
http://dx.doi.org/10.1002/(SICI)1521-3773(19981002)37:18<2490::AID-ANIE2490>3.0.CO;2-X

[17]. Ablialimov, O.; Kedziorek, M.; Torborg, C.; Malinska, M.; Wozniak, K.; Grela, K. Organometallics 2012, 31, 7316-7319.
http://dx.doi.org/10.1021/om300783g

[18]. Palencia, H.; Garcia-Jimenez, F.; Takacs, J. M. Tetrahedron Lett. 2004, 45, 3849-3853.
http://dx.doi.org/10.1016/j.tetlet.2004.03.138

[19]. Faller, J. W.; Fontaine, P. P. Organometallics 2006, 25, 5887-5893.
http://dx.doi.org/10.1021/om060650x

[20]. Tornatzky, J.; Kannenberg, A.; Blechert, S. Dalton Trans. 2012, 41, 8215-8225.
http://dx.doi.org/10.1039/c2dt30256j

[21]. Bouhrara, M.; Jeanneau, E.; Veyre, L.; Copereta, C.; Thieuleux, C. Dalton Trans. 2011, 42, 2995-2999.
http://dx.doi.org/10.1039/c0dt00932f

[22]. Truscott, B. J.; Klein, R.; Kaye, P. T. Tetrahedron Lett. 2010, 51, 5041-5043.
http://dx.doi.org/10.1016/j.tetlet.2010.07.097

[23]. Downing, S. P.; Danopoulos, A. A. Organometallics 2006, 25, 1337-1340.
http://dx.doi.org/10.1021/om051017z

[24]. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440-1449.
http://dx.doi.org/10.1021/ar800020y

[25]. Liu, J.; Chen, J.; Zhao, J.; Zhao, Y.; Li, L.; Zhang, H. Synthesis 2003, 17, 2661-2666.

[26]. Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972-975.
http://dx.doi.org/10.1021/om9709704

[27]. Fantasia, S.; Nolan, S. P. Chem. Eur. J. 2008, 14, 6987-6993.

[28]. Huynh, H. V.; Han, Y.; Ho, J. H. H.; Tan, G. K. Organometallics 2006, 25, 3267-3274.
http://dx.doi.org/10.1021/om060151w

[29]. Han, Y.; Hong, Y. T.; Huynh, H. V. J. Organomet. Chem. 2008, 693 (19), 3159-3165.
http://dx.doi.org/10.1016/j.jorganchem.2008.06.037

[30]. Shi, M.; Qian, H. X. Tetrahedron 2005, 61, 4949-4955.
http://dx.doi.org/10.1016/j.tet.2005.03.043

[31]. Paulose, T. A. P.; Olson, J. A.; Quail, J. W.; Foley, S. R. J. Organomet. Chem. 2008, 693(21-22), 3405-3410.
http://dx.doi.org/10.1016/j.jorganchem.2008.07.040

[32]. Chartoire, A.; Lesieur, M.; Falivene, L.; Slawin, A. M. Z.; Cavallo, L.; Cazin, C. S. J.; Nolan, S. P. Chem. - Eur. J. 2012, 18, 4517-4521, S4517/1-S4517/25.

[33]. Organ, M. G.; Calimsiz, S.; Sayah, M.; Hoi, K. H.; Lough, A. J. Angew. Chem. Int. Ed. 2009, 48, 2383-2387.
http://dx.doi.org/10.1002/anie.200805661

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