Nickel-Catalyzed Selective Cross-Coupling of Chlorosilanes with Organoaluminum Reagents
Corresponding Author
Dr. Yuki Naganawa
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorDr. Haiqing Guo
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorKei Sakamoto
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorCorresponding Author
Dr. Yumiko Nakajima
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorCorresponding Author
Dr. Yuki Naganawa
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorDr. Haiqing Guo
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorKei Sakamoto
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorCorresponding Author
Dr. Yumiko Nakajima
Interdisciplinary Research Center for Catalytic Chemistry, National Institute of Advanced Industrial Science and Technology Tsukuba, Ibaraki, 305-8565 Japan
Search for more papers by this authorGraphical Abstract
Nickel does the trick: Nickel-catalyzed cross-coupling reactions of chlorosilanes with organoaluminum reagents were developed. An electron-rich Ni(0)/PCy3 complex was found to be an effective catalyst for the desired transformation. The selective synthesis of a series of alkylmonochlorosilanes from di- and trichlorosilanes was achieved using the present catalytic systems.
Abstract
Nickel-catalyzed cross-coupling reactions of chlorosilanes with organoaluminum reagents were developed. An electron-rich Ni(0)/PCy3 complex was found to be an effective catalyst for the desired transformation. The reaction of dichlorosilanes 1 proceeded to give the corresponding monosubstituted products 2. Trichlorosilanes 4 underwent selective double substitution to furnish the corresponding monochlorosilanes 2. Overall, the selective synthesis of a series of alkylmonochlorosilanes 2 from di- and trichlorosilanes was achieved using the present catalytic systems.
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References
- 1
- 1aS. J. Clarson, M. J. Owen, S. D. Smith, M. E. Van Dyke, Advances in Silicones and Silicone-Modified Materials; American Chemical Society: Washington, DC, 2010;
- 1bJ. E. Mark, D. W. Schaefer, G. Lin, The Polysiloxanes; Oxford University Press: New York, 2015.
- 2Si−Cl bond forming reactions have been also reported as a means of the preparation of organochlorosilanes. Examples, see:
- 2aW. Wang, Y. Tan, Z. Xie, Z. Zhang, J. Organomet. Chem. 2014, 769, 29;
- 2bV. Pongkittiphan, E. A. Theodorakis, W. Chavasiri, Tetrahedron Lett. 2009, 50, 5080.
- 3
- 3aM. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley-Interscience: New York, 2000;
- 3bE. G. Rochow, W. F. Gilliam, J. Am. Chem. Soc. 1945, 67, 1772;
- 3cW. Patnode, D. F. Wilcock, J. Am. Chem. Soc. 1946, 68, 358;
- 3dC. Krüger, E. G. Rochow, Inorg. Chem. 1963, 2, 1295;
- 3eD. Seyferth, Organometallics 2001, 20, 4978.
- 4
- 4aB. T. Nguyen, C. J. Bedbury, J. P. Cannady, WO2003084967 A1, 2003;
- 4bB. T. Nguyen, WO2005068476 A1, 2005;
- 4cD. C. Bauer, C. J. Bedbury, B. T. Nguyen, WO2006083665 A1, 2005.
- 5
- 5aB. Wrackmeyer, E. Khan, W. Z. Milius, Naturforscher 2008, 63b, 1267;
- 5bM. Ochiai, E. Akiyama, Trans. Mater. Res. Soc. Jpn. 2012, 37, 451;
- 5cS. D. Rosenberg, J. J. Wakburn, H. E. Ramsden, J. Org. Chem. 1957, 22, 1606;
- 5dA. Tuulmets, A. Ploom, D. Panov, J. Järv, Synlett 2010, 291;
- 5eU. Pöschl, K. Hassler, Organometallics 1995, 14, 4948.
- 6S. Bähr, W. Xue, M. Oestreich ACS Catal. 2019, 9, 16.
- 7
- 7aH. Yamashita, T. Kobayashi, T. Hayashi, M. Tanaka, Chem. Lett. 1991, 20, 761;
- 7bH. Yamashita, M. Tanaka, M. Goto, Organometallics 1997, 16, 4696.
- 8
- 8aJ. R. McAtee, S. E. S. Martin, D. T. Ahneman, K. A. Johnson, D. A. Watson, Angew. Chem. Int. Ed. 2012, 51, 3663,
- 8bS. E. S. Martin, D. A. Watson, J. Am. Chem. Soc. 2013, 135, 13330;
- 8cJ. R. McAtee, S. E. S. Martin, A. P. Cinderella, W. B. Reid, K. A. Johnson, D. A. Watson, Tetrahedron 2014, 70, 4250;
- 8dB. Vulovic, D. A. Watson, Eur. J. Org. Chem. 2017, 4996.
- 9A. P. Cinderella, B. Vulovic, D. A. Watson, J. Am. Chem. Soc. 2017, 139, 7741.
- 10B. Vulovic, A. P. Cinderella, D. A. Watson, ACS Catal. 2017, 7, 8113.
- 11K. Matsumoto, J. Huang, Y. Naganawa, H. Guo, T. Beppu, K. Sato, S. Shimada, Y. Nakajima, Org. Lett. 2018, 20, 2481.
- 12
- 12aJ. K. Stille, K. S. Y. Lau, J. Am. Chem. Soc. 1976, 98, 5841;
- 12bH. Yamashita, T. Hayashi, T. Kobayashi, M. Tanaka, M. Goto, J. Am. Chem. Soc. 1988, 110, 4417;
- 12cA. A. Zlota, F. Frolow, D. Milstein, J. Chem. Soc. Chem. Commun. 1989, 1826;
- 12dS. Gatard, C.-H. Chen, B. M. Foxman, O. V. Ozerov, Organometallics 2008, 27, 6257.
- 13
- 13aR. Wakabayashi, K. Kawahara, K. Kuroda, Angew. Chem. Int. Ed. 2010, 49, 5273,
- 13bR. Wakabayashi, Y. Sugiura, T. Shibue, K. Kuroda, Angew. Chem. Int. Ed. 2011, 50, 10708,
- 14Reviews, see:
- 14aE.-I. Negishi, Aldrichimica Acta 2005, 38, 71;
- 14bE.-I. Negishi, Bull. Chem. Soc. Jpn. 2007, 80, 233;
- 14cP. Knochel, T. Blümke, K. Groll, Y. H. Chen , Top. Organomet. Chem. 2013, 41, 173;
- 14dP. von Zezschwitz , Top. Organomet. Chem. 2013, 41, 245.
- 15Selected examples of cross coupling with organoaluminum reagents, see:
- 15aT. Okita, K. Muto, J. Yamaguchi, Org. Lett. 2018, 20, 3132;
- 15bH. Ogawa, Z.-K. Yang, H. Minami, K. Kojima, T. Saito, C. Wang, M. Uchiyama, ACS Catal. 2017, 7, 3988;
- 15cX. Liu, C.-C. Hsiao, I. Kalvet, M. Leiendecker, L. Guo, F. Schoenebeck, M. Rueping, Angew. Chem. Int. Ed. 2016, 55, 6093,
- 15dR. Shang, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2015, 137, 7660;
- 15eT. Morioka, A. Nishizawa, K. Nakamura, M. Tobisu, N. Chatani, Chem. Lett. 2015, 44, 1729;
- 15fK. Groll, T. D. Blümke, A. Unsinn, D. Haas, P. Knochel, Angew. Chem. Int. Ed. 2012, 51, 11157,
- 15gD. B. Biradar, H.-M. Gau, Chem. Commun. 2011, 47, 10467;
- 15hS. Kawamura, K. Ishizuka, H. Takaya, M. Nakamura, Chem. Commun. 2010, 46, 6054;
- 15iH. Gao, P. Knochel, Synlett 2009, 1321;
- 15jW.-T. Shu, S. Zhou, H.-M. Gau, Synthesis 2009, 4075.
- 16
- 16aL. N. Lewis, J. Stein, Y. Gao, R. E. Colborn, G. Hutchins, Platinum Met. Chem. 1997, 41, 66;
- 16bY. Nakajima, S. Shimada, RSC Adv. 2015, 5, 20603;
- 16cD. Troegel, J. Stohrer, Coord. Chem. Rev. 2011, 255, 1440;
- 16dB. G. Marciniec, Coord. Chem. Rev. 2005, 249, 2374;
- 16eD. Xiaoyong, H. Zheng, ACS Catal. 2017, 7, 1227.
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