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M. Murata et al.
PAPER
References
1H NMR (CDCl3): d = 0.77 (s, 3 H), 2.30 (s, 3 H), 6.43 (dd, J = 1.8,
3.0 Hz, 2 H), 6.79 (d, J = 3.0 Hz, 2 H), 7.10 (d, J = 8.0 Hz, 2 H),
7.62 (d, J = 8.0 Hz, 2 H), 7.73 (d, J = 1.8 Hz, 2 H).
(1) (a) Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem.
1997, 62, 6458. (b) Murata, M.; Oyama, T.; Watanabe, S.;
Masuda, Y. J. Org. Chem. 2000, 65, 164. (c) Baudoin, O.;
Guénard, D.; Guéritte, F. J. Org. Chem. 2000, 65, 9268.
(d) Broutin, P.-E.; Čerña, I.; Campaniello, M.; Leroux, F.;
Colobert, F. Org. Lett. 2004, 6, 4419.
13C NMR (CDCl3): d = –4.41, 21.17, 109.68, 120.75, 122.78,
128.94, 131.44, 136.02, 147.88, 152.18, 169.30.
HRMS (EI): m/z calcd for C17H16O4Si [M+]: 312.0818; found:
(2) (a) Murata, M.; Suzuki, K.; Watanabe, S.; Masuda, Y. J.
Org. Chem. 1997, 62, 8569. (b) Manoso, A. S.; DeShong, P.
J. Org. Chem. 2001, 66, 7455. (c) Murata, M.; Ishikura, M.;
Nagata, M.; Watanabe, S.; Masuda, Y. Org. Lett. 2002, 4,
1843. (d) Komuro, K.; Ishizaki, K.; Suzuki, H. Touagousei-
kenkyu-nenpo 2003, 6, 24.
312.0845.
3eg
1H NMR (CDCl3): d = 0.79 (s, 3 H), 6.44 (dd, J = 3.6, 1.2 Hz, 2 H),
6.78 (d, J = 3.6 Hz, 2 H), 7.36 (d, J = 8.3 Hz, 2 H), 7.53 (d, J = 8.3
Hz, 2 H), 7.73 (d, J = 1.2 Hz, 2 H).
(3) Nakamura, T.; Kinoshita, H.; Shinokubo, H.; Oshima, K.
Org. Lett. 2002, 4, 3165.
(4) Murata, M.; Watanabe, S.; Masuda, Y. Synlett 2000, 1043.
(5) (a) Murata, M.; Watanabe, S.; Masuda, Y. Tetrahedron Lett.
1999, 40, 9255. (b) Denmark, S. E.; Kallemeyn, J. M. Org.
Lett. 2003, 5, 3483.
(6) The silylation using trialkylsilanes was reported, however,
no example of diarylmethylsilanes was provided, see:
Yamanoi, Y. J. Org. Chem. 2005, 70, 9607.
(7) The Chemistry of Organic Silicon Compounds; Patai, S.;
Rappoport, Z., Eds.; Wiley & Sons: New York, 2000.
(8) For examples of coupling reactions of aryl nonaflates, see:
(a) Rottlander, M.; Knochel, P. J. Org. Chem. 1998, 63, 203.
(b) Anderson, K. W.; Mendez-Perez, M.; Priego, J.;
Buchwald, S. L. J. Org. Chem. 2003, 68, 9563.
13C NMR (CDCl3): d = –4.49, 109.71, 123.19, 128.25, 132.25,
136.02, 136.41, 147.98, 154.38.
HRMS (EI): m/z calcd for C15H13O235ClSi [M+]: 288.0373; found:
288.0418.
3eh
1H NMR (CDCl3): d = 0.85 (s, 3 H), 6.43 (dd, J = 1.2, 3.7 Hz, 2 H),
6.83 (d, J = 3.7 Hz, 2 H), 7.23 (dd, J = 4.9, 3.1 Hz, 1 H), 7.43 (d,
J = 3.1 Hz, 1 H), 7.69 (d, J = 4.9 Hz, 1 H), 7.73 (d, J = 1.2 Hz, 2 H).
13C NMR (CDCl3): d = –3.24, 109.47, 109.73, 123.07, 128.34,
132.32, 137.00, 147.90, 154.45.
HRMS (EI): m/z calcd for C13H12O2SiS [M+]: 260.0327; found:
260.0368.
(9) (a) Itami, K.; Nokami, T.; Yoshida, J. J. Am. Chem. Soc.
2001, 123, 5600. (b) Itami, K.; Nokami, T.; Ishimura, Y.;
Mitsudo, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001,
123, 11577.
(10) Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 138.
(11) For examples of the cross-coupling reaction of other all-
carbon-substituted organosilanes, see: (a) Denmark, S. E.;
Choi, J. Y. J. Am. Chem. Soc. 1999, 121, 5821. (b) Nakao,
Y.; Oda, T.; Sahoo, A. K.; Hiyama, T. J. Organomet. Chem.
2003, 687, 570. (c) Trost, B. M.; Machacek, M. R.; Ball, Z.
T. Org. Lett. 2003, 5, 1895.
Palladium-Catalyzed Cross-Coupling of Aryl(2-furyl)silanes
A mixture of di(2-furyl)(methyl)phenylsilane (2 mmol) and
TBAF·3H2O (2 mmol) in dioxane–H2O (8:1, 3.6 mL) was stirred at
90 °C for 2 h. To this solution were added PdCl2(dppf) (0.05 mmol)
and 4-bromobenzotrifluoride (1.0 mmol). After stirring at 90 °C for
16 h, GC analysis of the resulting mixture indicated the formation
of 4-phenylbenzotrifluoride in 76% yield.
Rhodium-Catalyzed 1,4-Addition of Aryl(2-furyl)silanes to a,b-
Unsaturated Esters
A mixture of di(2-furyl)(methyl)phenylsilane (2 mmol) and
TBAF·3H2O (2 mmol) in dioxane–H2O (8:1, 3.6 mL) was stirred at
90 °C for 2 h. To this solution were added [Rh(OH)(cod)]2 (0.025
mmol) and tert-butyl acrylate (1.0 mmol). After stirring at 90 °C for
16 h, GC analysis of the resulting mixture indicated the formation
of tert-butyl 3-phenylpropionate in 80% yield.
(12) Cross-coupling of aryltri(2-furyl)germanes with aryl halides
has been reported, see ref. 3.
(13) (a) Huang, T. S.; Li, C. J. Chem. Commun. 2001, 2348.
(b) Mori, A.; Danda, Y.; Fujii, T.; Hirabayashi, K.; Osakada,
K. J. Am. Chem. Soc. 2001, 123, 10774. (c)Fujii, T.;Koike,
T.; Mori, A.; Osakada, K. Synlett 2002, 298. (d) Koike, T.;
Du, X.; Mori, A.; Osakada, K. Synlett 2002, 301. (e) Oi, S.;
Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667. (f) Murata,
M.; Shimazaki, R.; Ishikura, M.; Watanabe, S.; Masuda, Y.
Synthesis 2002, 717.
(14) To some extent a plausible mechanism can be derived from
that proposed by us for triethoxysilane (see ref. 2a);
however, the role of KI (Table 2, entries 9–12) is not easily
interpreted.
Acknowledgment
This work was supported by a Grant-in-Aid for Encouragement of
Young Scientists (B) from the Ministry of Education, Culture,
Sports, Science and Technology, Japan (No. 16750069). We also
acknowledge the Akiyama Foundation, and Taisho Pharmaceutical
Award from The Society of Synthetic Organic Chemistry, Japan,
for additional financial support.
(15) Cunico, R. F.; Bedell, L. J. Org. Chem. 1980, 45, 4797.
Synthesis 2006, No. 11, 1771–1774 © Thieme Stuttgart · New York