160
9 Carbon-Carbon Cross-Coupling Reactions
Various experimental investigations have revealed that the microwave irradiation
induces defects into the graphene that can range from monovacancy to larger voids.
These defects strongly bind the Pd clusters/nanoparticles that act as the catalyst.
More important is the role of the support as the theoretical investigations demonstrate that the resulting metal-ligand interaction promotes electron flow between the
metal cluster and the defected graphene. This is clearly due to the conductive nature
of the support that facilitates any charge transfer to and from the reactants. However,
the benefit of the support substrate is diminished if the metal is weakly immobilized.
Preliminary theoretical results have found that graphene may also lower the activation
energy of Ni n clusters. These studies indicate that a bifunctional catalyst combining
Ni and Pd where different reaction steps could be performed by different metallic
sites may offer a more powerful catalyst. In addition to modifying the supporting
cluster, one can envision enhancing the catalytic activity by making the support as
a better donor/acceptor. This could be accomplished by doping the graphene with
atoms or attaching ligands. These are interesting directions that need further work.
References
1. C.A. Busacca, D.R. Fandrick, J.J. Song, C.H. Senanayake, Adv. Synth. Catal. 353, 1825–1864
(2011)
2. J. Magano, J.R. Dunetz, Chem. Rev. 111, 2177–2250 (2011)
3. I. Shinkai, A.O. King, R.D. Larsen, Pure Appl. Chem. 66, 1551 (1994)
4. I.P. Beletskaya, A.V. Cheprakov, in The Mizoroki–Heck Reaction, John Wiley & Sons, Ltd,
2009, pp. 51–132
5. A. Jutand, in The Mizoroki–Heck Reaction, John Wiley & Sons, Ltd, 2009, pp. 1–50
6. O. Bagheri, F. Sadegh, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. MohammadpoorBaltork, M. Safiri, Appl. Organomet. Chem. 28, 337–346 (2014)
7. R.J.P. Corriu, J. Organomet. Chem. 653, 20–22 (2002)
8. M.K. Das, J.A. Bobb, A.A. Ibrahim, A. Lin, K.M. AbouZeid, M.S. El-Shall, A.C.S. Appl,
Mater. Interfaces 12, 23844–23852 (2020)
9. C. Deraedt, D. Astruc, Acc. Chem. Res. 47, 494–503 (2014)
10. J. Derosa, V.T. Tran, V.A. van der Puyl, K.M. Engle, Aldrichim. Acta 51, 21–32 (2018)
11. E. Gioria, J. del Pozo, J.M. Martinez-Ilarduya, P. Espinet, Angew. Chem. Int. Ed. 55, 13276–
13280 (2016)
12. J.H. Hilmer, E. Champeil, M.K. Lakshman, Abstr. Pap. Am. Chem. Soc. 230, U3264–U3264
(2005)
13. S. Jadhav, A. Jagdale, S. Kamble, A. Kumbhar, R. Salunkhe, RSC Adv. 6, 3406–3420 (2016)
14. J.K. Kirsch, J.B. Johnson. Abstr. Pap. Am. Chem. Soc. 247 (2014)
15. A.H. Labulo, B.S. Martincigh, B. Omondi, V.O. Nyamori, J. Mater. Sci. 52, CP14–9248 (2017)
16. R.C. Larock, D.R. Leach, Organometallics 1, 74–81 (1982)
17. A. Lengar, C.O. Kappe, Org. Lett. 6, 771–774 (2004)
18. A. Leyva-Perez, Dalton Trans. 46, 15987–15990 (2017)
19. G. Li, R. Jin, Nanotechnology Reviews 2, 529–545 (2013)
20. M.I. Lipschutz, T.D. Tilley, Angew. Chem. Int. Ed. 53, 7290–7294 (2014)
21. M.-X. Liu, H.-P. Gong, Z.-J. Quan, X.-C. Wang, Synlett 29, 330–335 (2018)
22. J.C. Lo, J. Gui, Y. Yabe, C.-M. Pan, P.S. Baran, Nature 516, 343–348 (2014)
23. K. Mennecke, W. Solodenko, A. Kirschning, Synthesis-Stuttgart, 1589–1599 (2008)
9 Carbon-Carbon Cross-Coupling Reactions
Various experimental investigations have revealed that the microwave irradiation
induces defects into the graphene that can range from monovacancy to larger voids.
These defects strongly bind the Pd clusters/nanoparticles that act as the catalyst.
More important is the role of the support as the theoretical investigations demonstrate that the resulting metal-ligand interaction promotes electron flow between the
metal cluster and the defected graphene. This is clearly due to the conductive nature
of the support that facilitates any charge transfer to and from the reactants. However,
the benefit of the support substrate is diminished if the metal is weakly immobilized.
Preliminary theoretical results have found that graphene may also lower the activation
energy of Ni n clusters. These studies indicate that a bifunctional catalyst combining
Ni and Pd where different reaction steps could be performed by different metallic
sites may offer a more powerful catalyst. In addition to modifying the supporting
cluster, one can envision enhancing the catalytic activity by making the support as
a better donor/acceptor. This could be accomplished by doping the graphene with
atoms or attaching ligands. These are interesting directions that need further work.
References
1. C.A. Busacca, D.R. Fandrick, J.J. Song, C.H. Senanayake, Adv. Synth. Catal. 353, 1825–1864
(2011)
2. J. Magano, J.R. Dunetz, Chem. Rev. 111, 2177–2250 (2011)
3. I. Shinkai, A.O. King, R.D. Larsen, Pure Appl. Chem. 66, 1551 (1994)
4. I.P. Beletskaya, A.V. Cheprakov, in The Mizoroki–Heck Reaction, John Wiley & Sons, Ltd,
2009, pp. 51–132
5. A. Jutand, in The Mizoroki–Heck Reaction, John Wiley & Sons, Ltd, 2009, pp. 1–50
6. O. Bagheri, F. Sadegh, M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. MohammadpoorBaltork, M. Safiri, Appl. Organomet. Chem. 28, 337–346 (2014)
7. R.J.P. Corriu, J. Organomet. Chem. 653, 20–22 (2002)
8. M.K. Das, J.A. Bobb, A.A. Ibrahim, A. Lin, K.M. AbouZeid, M.S. El-Shall, A.C.S. Appl,
Mater. Interfaces 12, 23844–23852 (2020)
9. C. Deraedt, D. Astruc, Acc. Chem. Res. 47, 494–503 (2014)
10. J. Derosa, V.T. Tran, V.A. van der Puyl, K.M. Engle, Aldrichim. Acta 51, 21–32 (2018)
11. E. Gioria, J. del Pozo, J.M. Martinez-Ilarduya, P. Espinet, Angew. Chem. Int. Ed. 55, 13276–
13280 (2016)
12. J.H. Hilmer, E. Champeil, M.K. Lakshman, Abstr. Pap. Am. Chem. Soc. 230, U3264–U3264
(2005)
13. S. Jadhav, A. Jagdale, S. Kamble, A. Kumbhar, R. Salunkhe, RSC Adv. 6, 3406–3420 (2016)
14. J.K. Kirsch, J.B. Johnson. Abstr. Pap. Am. Chem. Soc. 247 (2014)
15. A.H. Labulo, B.S. Martincigh, B. Omondi, V.O. Nyamori, J. Mater. Sci. 52, CP14–9248 (2017)
16. R.C. Larock, D.R. Leach, Organometallics 1, 74–81 (1982)
17. A. Lengar, C.O. Kappe, Org. Lett. 6, 771–774 (2004)
18. A. Leyva-Perez, Dalton Trans. 46, 15987–15990 (2017)
19. G. Li, R. Jin, Nanotechnology Reviews 2, 529–545 (2013)
20. M.I. Lipschutz, T.D. Tilley, Angew. Chem. Int. Ed. 53, 7290–7294 (2014)
21. M.-X. Liu, H.-P. Gong, Z.-J. Quan, X.-C. Wang, Synlett 29, 330–335 (2018)
22. J.C. Lo, J. Gui, Y. Yabe, C.-M. Pan, P.S. Baran, Nature 516, 343–348 (2014)
23. K. Mennecke, W. Solodenko, A. Kirschning, Synthesis-Stuttgart, 1589–1599 (2008)