Iridium-Catalyzed Mizoroki–Heck-Type Reaction of Organosilicon Reagents
Tooru Koike
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorXiaoli Du
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorTomoyuki Sanada
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorYasuaki Danda
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorAtsunori Mori Prof. Dr.
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorTooru Koike
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorXiaoli Du
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorTomoyuki Sanada
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorYasuaki Danda
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorAtsunori Mori Prof. Dr.
Chemical Resources Laboratory Tokyo Institute of Technology 4259 Nagatsuta, Yokohama 226–8503, Japan, Fax: (+81) 45–924–5224
Search for more papers by this authorGraphical Abstract
Independent of substrate and solvent, the CC bond-forming reaction of organosilicon reagents with α,β-unsaturated carbonyl compounds can be catalyzed by an iridium complex to give exclusively the Mizoroki–Heck-type addition/elimination product (see scheme). This result sharply contrasts the analogous reaction with a rhodium catalyst under similar conditions in which the 1,4-addition product is obtained preferentially. cod=cycloocta-1,5-diene.
References
- 1
- 1aN. Chatani, S. Ikeda, K. Ohe, S. Murai, J. Am. Chem. Soc. 1992, 114, 9710–9711;
- 1bC.-H. Jun, Z. Lu, R. H. Crabtree, Tetrahedron Lett. 1992, 33, 7119–7120;
- 1cP. M. Maitlis, A. Haynes, G. I. Sunley, M. J. Howard, Dalton Trans., 1996, 2187–2196;
- 1dS.-I. Murahashi, H. Takaya, Acc. Chem. Res. 2002, 33, 225–233;
- 1eM. Murakami, K. Itami, M. Ubukata, I. Tsuji, Y. Ito, J. Org. Chem. 1998, 63, 4–5;
- 1fR. Takeuchi, M. Kashio, Angew. Chem. 1997, 109, 268–270;
10.1002/ange.19971090320 Google ScholarAngew. Chem. Int. Ed. Engl. 1997, 36, 263–265;
- 1gS. Sakaguchi, T. Kubo, Y. Ishii, Angew. Chem. 2001, 113, 2602–2604;
10.1002/1521-3757(20010702)113:13<2602::AID-ANGE2602>3.0.CO;2-M Google ScholarAngew. Chem. Int. Ed. 2001, 40, 2534–2536;10.1002/1521-3773(20010702)40:13<2534::AID-ANIE2534>3.0.CO;2-2 CAS PubMed Web of Science® Google Scholar
- 1hT. Ohmura, Y. Yamamoto, N. Miyaura, Organometallics 2000, 19, 365–367;
- 1iT. Shibata, K. Takagi, J. Am. Chem. Soc. 2000, 122, 9852–9853.
- 2B:
- 2aC. S. Cho, S. Uemura, J. Organomet. Chem. 1994, 465, 85–92;
- 2bX. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H.-F. Wang, K. Fugami, M. Kosugi, Org. Lett. 2001, 3, 3313–3316; Sn:
- 2cK. Fugami, S. Hagiwara, H. Oda, M. Kosugi, Synlett 1998, 477–478;
- 2dK. Hirabayashi, J. Ando, Y. Nishihara, A. Mori, T. Hiyama, Synlett 1999, 99–101; Si:
- 2eK. Hirabayashi, Y. Nishihara, A. Mori, T. Hiyama, Tetrahedron Lett. 1998, 39, 7893–7896;
- 2fK. Hirabayashi, J. Ando, J. Kawashima, Y. Nishihara, A. Mori, T. Hiyama, Bull. Chem. Soc. Jpn. 2000, 73, 1409–1417.
- 3B:
- 3aY. Takaya, M. Ogasawara, T. Hayashi, M. Sakai, N. Miyaura, J. Am. Chem. Soc. 1998, 120, 5579–5580;
- 3bM. Lautens, A. Roy, K. Fukuoka, K. Fagnou, B. Martin-Matúte, J. Am. Chem. Soc. 2001, 123, 5358–5359; Sn:
- 3cS. Oi, M. Moro, Y. Inoue Chem. Lett. 1998, 83–84;
- 3dY. Meng, C. J. Li, J. Am. Chem. Soc. 2000, 122, 9538–9539; Si:
- 3eA. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada, J. Am. Chem. Soc. 2001, 123, 10 774–10 775;
- 3fT. Koike, X. Du, A. Mori, K. Osakada Synlett 2002, 301–303;
- 3gS. Oi, Y. Honma, Y. Inoue Org. Lett. 2002, 4, 667–669;
- 3hM. Murata, R. Shimazaki, M. Ishikura, S. Watanabe, Y. Masuda, Synthesis, 2002, 717–719;
- 3iT. S. Huang, C. J. Li, Chem. Commun. 2001, 2348–2349.
- 4B: E. J. Farrington, J. M. Brown, C. F. J. Barnard, E. Rowsell, Angew. Chem. 2002, 114, 169–171;
Angew. Chem. Int. Ed. 2002, 41, 161–163.
10.1002/1521-3773(20020104)41:1<161::AID-ANIE161>3.0.CO;2-N CAS PubMed Web of Science® Google Scholar
- 5Although the Mizoroki–Heck reaction of organic halides instead of an organometallic reagent with a rhodium or iridium catalyst is reported, a high temperature (150 °C) must be applied: S. Iyer, J. Organomet. Chem. 1995, 490, C 27–C28.
- 6X. Du, T. Koike, Y. Danda, A. Mori, unpublished results; a part of this work was presented at the 81st Annual Meeting of the Chemical Society of Japan, 4G644 (2002).
- 7
- 7aM. E. Mowery, P. DeShong, J. Org. Chem. 1999, 64, 1684–1688;
- 7bK. Tamao, K. Kobayashi, Y. Ito, Tetrahedron Lett. 1989, 30, 6051–6054;
- 7cK. Shibata, K. Miyazawa, Y. Goto, Chem. Commun. 1997, 1309–1310.
- 8Although we have examined other α,β-unsaturated carbonyl compounds bearing substituents at the α and/or β positions, no desired addition/elimination reaction product was obtained.
- 9H. Nakagawa, S. Sakaguchi, Y. Ishii, 81st Annual Meeting of the Chemical Society of Japan, 1G549 (2002). In our present study, the reaction of (4-MeC6H4)EtSi(OH)2 (0.3 mmol) with butyl acrylate 2 a (0.9 mmol) in toluene/H2O at 120 °C in the presence of [{Ir(OMe)(cod)}2] (3 mol %) afforded the Mizoroki–Heck-type product(46 %), in which 36 % of 2 a was converted into 9.
- 10The rhodium-catalyzed reaction under similar conditions (3 mol % of [{Rh(OH)(cod)}2], 4-MeC6H4SiEt(OH)2 (0.6 mmol), 2 a (0.3 mmol), and 3 b (0.6 mmol) in THF (3 mL) at 70 °C for 24 h) afforded 27 % of the Mizoroki–Heck-type product 3 a and 3 % of 4 b with 75 % recovery of 3 b.
