Table 3 One-pot double Hiyama coupling of aryl dichloridesa
were realized for the first time. We anticipate that the
application of this catalyst can be extended to other catalytic
processes.
This work was supported by the National Research
Foundation of Korea Grant funded by Korean Government
(2009-0072013), by the Carbon Dioxide R&D Center of the
21st Century Frontier R&D Programs, and by the National
Honor Scientist Program of the Ministry of Education,
Science and Technology in Korea.
Notes and references
1 (a) T. Hiyama, in Metal-Catalyzed Cross-Coupling Reactions,
ed. F. Diederich and P. J. Stang, Wiley-VCH, New York, 1998,
ch. 10; (b) T. Hiyama, J. Organomet. Chem., 2002, 653, 58;
(c) S. E. Denmark and J. D. Baird, Chem.–Eur. J., 2006, 12, 4954.
2 (a) D. G. Hall, in Boronic Acids: Preparation and Applications in
Organic Synthesis and Medicine, Wiley-VCH, Weinheim, 2005;
(b) E. A. B. Kantchev, C. J. O’Brien and M. G. Organ, Angew.
Chem., Int. Ed., 2007, 46, 2768; (c) R. Martin and S. L. Buchwald,
Acc. Chem. Res., 2008, 41, 1461; (d) G. C. Fu, Acc. Chem. Res.,
2008, 41, 1555; (e) M. Tobisu and N. Chatani, Angew. Chem., Int.
Ed., 2009, 48, 3565.
3 (a) D. Milstein and J. K. Stille, J. Am. Chem. Soc., 1979, 101, 4992;
(b) P. Espinet and A. M. Echavarren, Angew. Chem., Int. Ed., 2004,
43, 4704.
a
4 For some recent developments in Hiyama reaction, see: (a) J.-Y. Lee
and G. Fu, J. Am. Chem. Soc., 2003, 125, 5616; (b) P. Pierrat,
P. Gros and Y. Fort, Org. Lett., 2005, 7, 697; (c) W. M. Seganish,
C. J. Handy and P. DeShong, J. Org. Chem., 2005, 70, 8948;
(d) T. Mino, Y. Shirae, T. Saito, M. Sakamoto and T. Fujita,
J. Org. Chem., 2006, 71, 9499; (e) J. Ju, H. Nam, M. H. Jung and
S. Lee, Tetrahedron Lett., 2006, 47, 8673; (f) N. A. Strotman,
S. Sommer and G. C. Fu, Angew. Chem., Int. Ed., 2007, 46, 3556;
(g) L. Zhang and J. Wu, J. Am. Chem. Soc., 2008, 130, 12250;
(h) C. M. So, H. W. Lee, C. P. Lau and F. Y. Kwong, Org. Lett.,
2009, 11, 317; (i) C. Dash, M. M. Shaikh and P. Ghosh, Eur. J.
Inorg. Chem., 2009, 1608.
Aryl dichloride (1.0 mmol), arylsilane (3.0 mmol), 2a (1.0 mol%),
NaOH (6.0 mmol), TBAB (1.0 mmol), H2O (4 ml), 80 1C.
5 (a) M. L. Clarke, Adv. Synth. Catal., 2005, 347, 303; (b) E. Alacid
and C. Najera, Adv. Synth. Catal., 2006, 348, 945;
´
(c) L. Ackermann, C. J. Gshrei, A. Althammer and M. Riederer,
Chem. Commun., 2006, 1419.
Scheme
2 One-pot multiple Hiyama coupling of 1,2,4,5-
tetrachlorobenzene.
6 (a) D. Srimani, S. Sawoo and A. Sarkar, Org. Lett., 2007, 9, 3639;
(b) S. Shi and Y. Zhang, J. Org. Chem., 2007, 72, 5927;
(c) B. C. Ranu, R. Dey and K. Chattopadhyay, Tetrahedron Lett.,
2008, 49, 3430.
7 (a) L. Bourget-Merle, M. F. Lappert and J. R. Severn, Chem. Rev.,
2002, 102, 3031; (b) P. L. Franceschini, M. Morstein, H. Berke and
H. W. Schmalle, Inorg. Chem., 2003, 42, 7273; (c) Y. Li, L. Wang,
H. Gao, F. Zhu and Q. Wu, Appl. Organomet. Chem., 2006, 20, 436;
(d) L.-M. Tang, Y.-Q. Duan, X.-F. Li and Y.-S. Li, J. Organomet.
Chem., 2006, 691, 2023; (e) P. L. Holland, Acc. Chem. Res., 2008, 41,
905; (f) A. Hadzovic and D. Song, Organometallics, 2008, 27, 1290.
8 (a) A. F. Pozharskii, A. T. Spldartenko and A. Katritzky,
Heterocycles in Life and Society, Wiley, New York, 1997;
(b) E. Tyrell and P. Brookes, Synthesis, 2004, 469.
Scheme 3 One-pot Hiyama–Heck double coupling.
9 (a) M. Feuerstein, H. Doucet and M. Santelli, J. Organomet. Chem.,
2003, 687, 327; (b) T. Itoh, K. Sato and T. Mase, Adv. Synth. Catal.,
2004, 346, 1859; (c) N. Kudo, M. Perseghini and G. C. Fu, Angew.
Chem., Int. Ed., 2006, 45, 1282; (d) K. L. Billingsley,
K. W. Anderson and S. L. Buchwald, Angew. Chem., Int. Ed.,
2006, 45, 3484; (e) I. J. S. Fairlamb, Chem. Soc. Rev., 2007, 36, 1036;
(f) C. A. Fleckenstein and H. Plenio, J. Org. Chem., 2008, 73, 3236.
In conclusion, we have demonstrated that the
b-diketiminatophosphane Pd complex serves as a highly active
catalyst for the Hiyama coupling reaction of a wide range of
aryl chlorides with aryltriethoxysilanes in water. Notably, the
efficient one-pot double Hiyama couplings of aryl dichlorides
c
9048 Chem. Commun., 2010, 46, 9046–9048
This journal is The Royal Society of Chemistry 2010