Domino Catalysis: Palladium-Catalyzed Carbonylation of Allylic Alcohols to β,γ-Unsaturated Esters†
Dr. Qiang Liu
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorLipeng Wu
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorDr. Haijun Jiao
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorXianjie Fang
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorDr. Ralf Jackstell
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Beller
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)Search for more papers by this authorDr. Qiang Liu
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorLipeng Wu
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorDr. Haijun Jiao
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorXianjie Fang
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorDr. Ralf Jackstell
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Search for more papers by this authorCorresponding Author
Prof. Dr. Matthias Beller
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)
Leibniz-Institut für Katalyse an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock (Germany)Search for more papers by this authorThe research has been funded by the State of Mecklenburg-Western Pomerania, the BMBF, and the DFG (Leibniz Prize). We thank Dr. W. Baumann, Dr. C. Fischer, S. Buchholz, S. Schareina, A. Koch, and S. Rossmeisl (all at LIKAT) for their excellent technical and analytical support. Q.L. thanks the Alexander von Humboldt Foundation for financial support.
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References
- 1
- 1aM. Beller, Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1, 2nd ed., Wiley-VCH, Weinheim, 2002, pp. 145–156;
- 1bA. Brennführer, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 4176–4196;
10.1002/ange.200900013 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 4114–4133;
- 1cX.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, 4986–5009;
- 1dX.-F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, 1–35.
- 2
- 2aE. Wenkert, B. L. Buckwalter, S. S. Sathe, Synth. Commun. 1973, 3, 261–264;
- 2bK. N. Houk, Chem. Rev. 1976, 76, 1–74;
- 2cD. Armesto, M. J. Ortiz, A. R. Agarrabeitia, CRC Handbook of Organic Photochemistry and Photobiology, 2nd ed., CRC, Boca Raton, FL, 2004, pp. 77/71–77/11;
- 2dG. B. Bajracharya, P. S. Koranne, R. N. Nadaf, R. K. M. Gabr, K. Takenaka, S. Takizawa, H. Sasai, Chem. Commun. 2010, 46, 9064–9066;
- 2eM. Martin-Fontecha, A. R. Agarrabeitia, M. J. Ortiz, D. Armesto, Org. Lett. 2010, 12, 4082–4085.
- 3
- 3aC. Bruneau, J.-L. Renaud, B. Demerseman, Chem. Eur. J. 2006, 12, 5178–5187;
- 3bZ. Lu, S. Ma, Angew. Chem. 2008, 120, 264–303; Angew. Chem. Int. Ed. 2008, 47, 258–297;
- 3cM. Bandini, M. Tragni, Org. Biomol. Chem. 2009, 7, 1501–1507;
- 3dM. Bandini, Angew. Chem. 2011, 123, 1026–1027; Angew. Chem. Int. Ed. 2011, 50, 994–995;
- 3eB. Sundararaju, M. Achard, C. Bruneau, Chem. Soc. Rev. 2012, 41, 4467–4483.
- 4
- 4aW. T. Dent, R. Long, G. H. Whitfield, J. Chem. Soc. 1964, 1588–1594;
- 4bJ. Tsuji, J. Kiji, S. Imamura, M. Morikawa, J. Am. Chem. Soc. 1964, 86, 4350–4353;
- 4cT. Okano, N. Okabe, J. Kiji, Bull. Chem. Soc. Jpn. 1992, 65, 2589–2593;
- 4dA. Yamamoto, Bull. Chem. Soc. Jpn. 1995, 68, 433–446;
- 4eJ. Kiji, T. Okano, Y. Higashimae, Y. Fukui, Bull. Chem. Soc. Jpn. 1996, 69, 1029–1031;
- 4fS. Tommasi, S. Perrone, F. Rosato, A. Salomone, L. Troisi, Synthesis 2012, 423–430.
- 5
- 5aJ. Tsuji, K. Sato, H. Okumoto, J. Org. Chem. 1984, 49, 1341–1344;
- 5bT.-a. Mitsudo, N. Suzuki, T. Kondo, Y. Watanabe, J. Org. Chem. 1994, 59, 7759–7765.
- 6
- 6aY. Koyasu, H. Matsuzaka, Y. Hiroe, Y. Uchida, M. Hidai, J. Chem. Soc. Chem. Commun. 1987, 575–576;
- 6bS. Murahashi, Y. Imada, Y. Taniguchi, S. Higashiura, Tetrahedron Lett. 1988, 29, 4945–4948;
- 6cH. Matsuzaka, Y. Hiroe, M. Iwasaki, Y. Ishii, Y. Koyasu, M. Hidai, J. Org. Chem. 1988, 53, 3832–3838;
- 6dM. Iwasaki, Y. Kobayashi, J. P. Li, H. Matsuzaka, Y. Ishii, M. Hidai, J. Org. Chem. 1991, 56, 1922–1927;
- 6eS. Murahashi, Y. Imada, Y. Taniguchi, S. Higashiura, J. Org. Chem. 1993, 58, 1538–1545.
- 7R. Takeuchi, Y. Akiyama, J. Organomet. Chem. 2002, 651, 137–145.
- 8
- 8aY. Takahashi, K. Tsukiyama, S. Sakai, Y. Ishii, Tetrahedron Lett. 1970, 11, 1913–1916;
10.1016/S0040-4039(01)98116-X Google Scholar
- 8bT. Yamamoto, O. Saito, A. Yamamoto, J. Am. Chem. Soc. 1981, 103, 5600–5602.
- 9
- 9aJ. F. Knifton, J. Organomet. Chem. 1980, 188, 223–236;
- 9bH. Alper, I. Amer, J. Mol. Catal. 1989, 54, L33–L36;
- 9cK. Itoh, N. Hamaguchi, M. Miura, M. Nomura, J. Mol. Catal. 1992, 75, 117–122;
- 9dR. Naigre, H. Alper, J. Mol. Catal. A 1996, 111, 11–15;
- 9eM. Sakamoto, I. Shimizu, A. Yamamoto, Bull. Chem. Soc. Jpn. 1996, 69, 1065–1078;
- 9fT. Satoh, M. Ikeda, Y. Kushino, M. Miura, M. Nomura, J. Org. Chem. 1997, 62, 2662–2664;
- 9gW.-J. Xiao, H. Alper, J. Org. Chem. 1998, 63, 7939–7944;
- 9hM. J. Payne, D. J. Cole-Hamilton, J. Chem. Soc. Dalton Trans. 1997, 3167–3175.
- 10Under the optimized conditions (3–5 mol % of Pd(OAc)2, 12–20 mol % of PPh3) reported in Ref. [9f] and [9g], the carbonylation reactions of allylic alcohols with aliphatic alchohols provide very low yields according to the results reported in Ref. [9f] and our own experimental results. Please see the Supporting information for details.
- 11
- 11aD. Banerjee, R. V. Jagadeesh, K. Junge, H. Junge, M. Beller, Angew. Chem. 2012, 124, 11724–11728; Angew. Chem. Int. Ed. 2012, 51, 11556–11560;
- 11bD. Banerjee, R. V. Jagadeesh, K. Junge, H. Junge, M. Beller, ChemSusChem 2012, 5, 2039–2044.
- 12
- 12aA. Ajamian, J. L. Gleason, Angew. Chem. 2004, 116, 3842–3848;
10.1002/ange.200301727 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 3754–3760;
- 12bD. Enders, M. R. M. Huettl, C. Grondal, G. Raabe, Nature 2006, 441, 861–863;
- 12cA. Fürstner, Angew. Chem. 2009, 121, 1390–1393;
10.1002/ange.200805728 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 1364–1367.
- 13
- 13aC. Amatore, A. Jutand, M. A. M’Barki, Organometallics 1992, 11, 3009–3013;
- 13bC. Amatore, E. Carre, A. Jutand, M. A. M’Barki, Organometallics 1995, 14, 1818–1826.