Palladium- and Copper-Catalyzed Aryl Halide Amination ...

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20 J. E. R. Sadig, M. C. Willis REVIEW Me I Scheme 67 thiocarbamates, which were formed in situ under basic conditions, readily underwent copper-catalyzed intramolecular carbon–sulfur bond formation. Thiophenols and phenols showed the greatest reactivity; however, the corresponding alkyl series could also be employed, albeit to generate the products in reduced yields (Scheme 68). 73% + Scheme 68 4.3 Oxathioles Bao and co-workers reported a novel one-pot synthesis of 2-iminobenzo-1,3-oxathioles using a cascade addition/ intramolecular carbon–sulfur coupling process. 135 o-Iodophenols and isothiocyanates were combined using a copper(I) iodide/phenanthroline catalyst system to afford the desired heterocycles in good to excellent yields. A representative example is shown in Scheme 69. Scheme 69 H N 5 Conclusion I S NCS + Br HS Ph N S OPh S HNEt3 CuI (5 mol%) (10 mol%) 126 OMe K 2CO 3 DMSO, 90 °C 126 NH2 NH2 CuI (5 mol%) 1,10-phenanthroline (10 mol%) K2CO 3 dioxane, 90 °C N SBn S 69% (iodo substrate) By definition, palladium- and copper-catalyzed aryl amination, aryl etherification and aryl thioetherification reactions are transformations designed to fashion bonds between heteroatoms and aromatic rings. It is perhaps not surprising that these reactions have enjoyed considerable success when applied to the synthesis of aromatic heterocycles. The examples presented above show how these re- Synthesis 2011, No. 1, 1–22 © Thieme Stuttgart · New York Me OH CuI (10 mol%) 1,10-phenanthroline O SCN + I OMe (20 mol%) Cs2CO3 toluene, 70–90 °C S 86% Cl 72% N S Ar = 4-MeOC 6H 4 N S 76% N S 54% N O SPh SAr Ph OMe actions have been exploited towards a wide range of heterocyclic targets. They also show these reactions being used to provide new entries to existing, classic synthetic routes, as well as in the formulation of completely new disconnections. As advances in the underpinning transformations continue to develop – new coupling partners, more active catalysts and milder reaction conditions – the number of applications will undoubtedly continue to grow. The importance of heteroaromatic molecules virtually assures it. References (1) Palladium in Heterocyclic Chemistry, 1st ed.; Li, J. J.; Gribble, G. W., Eds.; Elsevier: Oxford, 2000. (2) Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127. (3) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285. (4) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873. (5) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644. (6) Palladium in Heterocyclic Chemistry, 2nd ed.; Li, J. J.; Gribble, G. W., Eds.; Elsevier: Oxford, 2007. (7) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395. (8) Willis, M. C. Tetrahedron 2009, 65, 8907. (9) Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927. (10) (a) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. Int. Ed. 1995, 34, 1348. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133. (d) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215. (11) (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969. (b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609. (c) Hartwig, J. F.; Richards, S.; Barañano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626. (d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217. (12) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382. (13) Goldberg, I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. (14) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1; Negishi, E. I., Ed.; Wiley- Interscience: New York, 2002, 1051–1096. (15) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross- Coupling Reactions, 2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004. (16) Surry, D. S.; Buchwald, S. L. Angew. Chem. Int. Ed. 2008, 47, 6338. (17) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534. (18) Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400; Corrigendum: Angew. Chem. Int. Ed. 2004, 43, 1043. (19) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337. (20) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. (21) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450. (22) Monnier, F.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 6954. (23) Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13. (24) Although the majority of examples described in this approach do not lead directly to an aromatic heterocycle, but to an intermediate, it is included because of its historical relevance to the development of palladium-catalyzed aryl halide amination chemistry in heterocycle synthesis. (25) (a) Wagaw, A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621. (b) Wagaw, A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
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