Abstract
The previous chapters have highlighted the positive impact that Pd-catalyzed cross-coupling reactions have had on the chemical sciences. The use of substrates that are pre-functionalized with a carbon–halogen bond allows for a high degree of regiocontrol since the Pd(0) catalyst has a high propensity to undergo oxidative addition at this site. However, these reactions become less predictable once more than one carbon–halogen bond is present in the substrate.
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Notes
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The use of pseudohalides (i.e. OTf or OTs) can also be used to impart selectivity.
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Reference [6].
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Complex 4.68 could also be generated in 85% by treatment of 4.65 with BzCl in pentane at RT for 1 h.
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Reference [29].
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Reference [32].
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Reference [36].
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Reference [37].
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Reference [39].
References
Petrone, D.A., Le, C.M., Newman, S.G., Lautens, M.: Pd-Catalyzed carboiodination: early developments to recent advancements (Chap. 7). In: Colacot, T. (ed.) New Trends in Cross-Coupling. The Royal Society of Chemistry, Cambridge (2015)
Petrone, D.A., Lischka, M., Lautens, M.: Angew. Chem. Int. Ed. 10652, 10635 (2013)
Schröter, S., Stock, C., Bach, T.: Tetrahedron 61, 2245 (2005)
Wang, J.-R., Manabe, K.: Synthesis 1405 (2009)
Fairlamb, I.J.S.: Chem. Soc. Rev. 36, 1036 (2007)
Minato, A., Suzuki, K., Tamao, K.: J. Am. Chem. Soc. 109, 1257 (1987)
Evans, D.A., Starr, J.T.: Angew. Chem. Int. Ed. 41, 1787 (2002)
Roush, W.R., Moriarty, K.J., Brown, B.B.: Tetrahedron Lett. 31, 6509 (1990)
Bellina, F., Carpita, A., de Santis, M.D., Rossi, R.: Tetrahedron Lett. 35, 6913 (1994)
Ratoveloamanana, V., Linstrumelle, G.: Tetrahedron Lett. 26, 2575 (1985)
Handy, S.T., Zhang, Y.: Chem. Commun. 299 (2006)
Legault, C.Y., Garcia, Y., Merlic, C.A., Houk, K.N.: J. Am. Chem. Soc. 129, 12664 (2007)
Garcia, Y., Schoenebeck, F., Legault, C.Y., Merlic, C.A., Houk, K.N.: J. Am. Chem. Soc. 131, 6632 (2009)
Kada, R., Knoppova, B., Kováč, P.: Collect. Czech. Chem. Commun. 49, 984 (1984)
Bach, T., Krüger, L.: Tetrahedron Lett. 39, 1729 (1998)
Conreaux, D., Bossharth, E., Monteiro, N., Desbordes, P., Vors, J., Balme, G.: Org. Lett. 9, 271 (2007)
Reyes, M.J., Castillo, R., Izquierdo, M.L., Alvarez-Builla, J.: Tetrahedron Lett. 47, 6457 (2006)
Fahey, D.R.: J. Am. Chem. Soc. 92, 402 (1970)
Just, G., Singh, R.J.: Org Chem. 54, 4453 (1989)
Hayashi, T., Niizuma, S., Kamikawa, T., Suzuki, N., Uozumi, Y.: J. Am. Chem. Soc. 117, 9101 (1995)
Lautens, M., Fang, Y.-Q.: Org. Lett. 5, 3679 (2003)
Saget, T., Perez, D., Cramer, N.: Org. Lett. 15, 1354 (2013)
Roy, A.H., Hartwig, J.F.: J. Am. Chem. Soc. 123, 1232 (2001)
Roy, A.H., Hartwig, J.F.: Organometallics 23, 1533 (2004)
Roy, A.H., Hartwig, J.F.: J. Am. Chem. Soc. 125, 13944 (2003)
Newman, S.G., Lautens, M.: J. Am. Chem. Soc. 132, 11416 (2010)
Nareddy, R., Mantilli, L., Guénée, L., Mazet, C.: Angew. Chem. Int. Ed. 51, 3826 (2013)
Quesnel, J.S., Arndtsen, B.A.: J. Am. Chem. Soc. 135, 16841 (2013)
Quesnel, J.S., Kayser, L.V., Fabrikant, A., Arndtsen, B.A.: Chem. Eur. J. 21, 9550 (2015)
Fahey, D.R.: J. Organomet. Chem. 27, 283 (1971)
Stambuli, J.P., Bühl, M., Hartwig, J.F.: J. Am. Chem. Soc. 124, 9346 (2002)
Lu, Z., Hu, C., Guo, J., Li, J., Cui, Y., Jia, Y.: Org. Lett. 12, 480 (2010)
Johansson Seechurn, C.C.C., Parisel, S.L., Colacot, T.J.: J. Org. Chem 76, 7918 (2011)
Li, H., Johansson Seechurn, C.C.C., Colacot, T.J.: ACS Catal. 2, 1147 (2012)
Pu, X., Li, H., Colacot, T.J.: J. Org. Chem. 78, 568 (2013)
Edgar, K.J., Falling, S.N.: J. Org. Chem. 55, 5287 (1990)
Flydare, J.A., et al.: 1-(chloromethyl)-2,3-hihydro-1H-benzo[e]indole dimer antibody-drug conjugate compounds, and methods of use and treatment. WO Patent 23355, A1 (2015)
Lulinski, P., Kryska, A., Sasnowski, M., Skulski, L.: Synthesis 3, 441 (2004)
Larock, R.C., Harrison, L.W.: J. Am. Chem. Soc. 106, 4218 (1984)
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Petrone, D.A. (2018). Harnessing Reversible Oxidative Addition: Application of Diiodinated Aromatic Compounds in Aryliodination. In: Stereoselective Heterocycle Synthesis via Alkene Difunctionalization. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-77507-4_4
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