LETTER
Pd-Catalyzed Coupling with Hexaarylcyclotrisiloxane
751
Itami, K.; Yoshida, J. Org. Lett. 2006, 8, 729; and references
cited therein. (q) Anderson, J. C.; Munday, R. H. J. Org.
Chem. 2004, 69, 8971. (r) Pierrat, P.; Gros, P.; Fort, Y. Org.
Lett. 2005, 7, 697. (s) Wolf, C.; Lerebours, R. Synthesis
2005, 2287. (t) Li, L.; Navasero, N. Org. Lett. 2006, 8, 3733.
(3) (a) Hirabayashi, K.; Mori, A.; Kawashima, J.; Suguro, M.;
Nishihara, Y.; Hiyama, T. J. Org. Chem. 2000, 65, 5342; and
references cited therein. (b) Koseki, Y.; Omino, K.; Anzai,
S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377.
(4) (a) Denmark, S. E.; Tymonko, S. A. J. Org. Chem. 2003, 68,
9151. (b) Denmark, S. E.; Baird, J. D. Chem. Eur. J. 2006,
12, 4954; and references cited therein. (c) Denmark, S. E.;
Neuville, L.; Christy, M. E. L.; Tymonko, S. A. J. Org.
Chem. 2006, 71, 8500.
(5) (a) Sahoo, A. K.; Nakao, Y.; Hiyama, T. Chem. Lett. 2004,
33, 632. (b) Shibata, K.; Miyazawa, K.; Goto, Y. Chem.
Commun. 1997, 1309. (c) Shukla, K. H.; Boehmler, D. J.;
Bogacyzk, S.; Duvall, B. R.; Peterson, W. A.; McElroy, W.
T.; DeShong, P. Org. Lett. 2006, 8, 4183; and references
cited therein. (d) Seganish, W. M.; Handy, C. J.; DeShong,
P. J. Org. Chem. 2005, 70, 8948; and references cited
therein. (e) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2,
2053. (f) Denmark, S. E.; Butler, C. R. Org. Lett. 2006, 8,
63; and references cited therein. (g) Koike, T.; Mori, A.
Synlett 2003, 1850; and references cited therein. (h) Itami,
K.; Mitsudo, K.; Nokami, T.; Kamei, T.; Koike, T.; Yoshida,
J. J. Organomet. Chem. 2002, 653, 105; and references cited
therein. (i) Denmark, S. E.; Pan, W. Org. Lett. 2002, 4, 4163;
and references cited therein. (j) Powell, D. A.; Fu, G. C. J.
Am. Chem. Soc. 2004, 126, 7788; and references cited
therein. (k) Wolf, C.; Lerebours, R.; Tanzini, E. H. Synthesis
2003, 2069. (l) Kabalka, G. W.; Dong, G.; Venkataiah, B.;
Chen, C. J. Org. Chem. 2005, 70, 9207.
attractive choice in the organosilicon-mediated arylation
with ready accessibility and stability of the reagent, easy
procedure in combination with no need of any special cat-
alysts, and atom-efficiency in the cross-coupling process.
Acknowledgment
Financial support provided by the Ministry of Education, Culture,
Sports, Science and Technology of Japan (Grants-in-Aid for
Scientific Research), Gunma Association of Silicon Science and
Technology (G-ASiST), and Sankyo Organic Chemicals Co. Ltd.
are gratefully acknowledged. The authors also thank Shin-Etsu
Chemical Co. Ltd. for generous gifts of diphenylsilanediol and
silicon tetrachloride.
References and Notes
(1) (a) Yoshida, J.; Tamao, K.; Takahashi, M.; Kumada, M.
Tetrahedron Lett. 1978, 2161. (b) Hatanaka, Y.; Hiyama, T.
Yuki Gosei Kagaku Kyokaishi 1990, 48, 834. (c) Hiyama,
T.; Hatanka, Y. Pure Appl. Chem. 1994, 66, 1471.
(d) Hatanaka, Y.; Goda, K.; Okahara, Y.; Hiyama, T.
Tetrahedron 1994, 50, 8301. (e) Hiyama, T. In Metal-
Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang,
P. J., Eds.; Wiley-VCH: Weinheim, 1998, 421–453.
(f) Hiyama, T.; Shirakawa, E. In Handbook of
Organopalladium Chemistry for Organic Synthesis;
Negishi, E., Ed.; John Wiley and Sons: New York, 2002,
285–309. (g) Hiyama, T.; Shirakawa, E. In Topics in
Current Chemistry, Vol. 219; Miyaura, N., Ed.; Springer:
Berlin, 2002, 61–85. (h) Hiyama, T. J. Organomet. Chem.
2002, 653, 58. (i) Denmark, S. E.; Sweis, R. F. Acc. Chem.
Res. 2002, 35, 835. (j) Denmark, S. E.; Sweis, R. F. Chem.
Pharm. Bull. 2002, 50, 1531. (k) Denmark, S. E.; Ober, M.
H. Aldrichimica Acta 2003, 36, 75. (l) Denmark, S. E.;
Sweis, R. F. In Metal-Catalyzed Cross-Coupling Reactions,
2nd ed.; de Meijere, A.; Diederich, F., Eds.; Wiley-VCH:
Weinheim, 2004, 163–216. (m) Spivey, A. C.; Gripton, C. J.
G.; Hannah, J. P. Curr. Org. Synth. 2004, 1, 211.
(6) (a) Seganish, W. M.; DeShong, P. Org. Lett. 2006, 8, 3951.
(b) Murata, M.; Shimazaki, R.; Watanabe, S.; Masuda, Y.
Synthesis 2001, 2231. (c) Lee, J.-Y.; Fu, G. C. J. Am. Chem.
Soc. 2003, 125, 5616. (d) Wolf, C.; Lerebours, R. Org. Lett.
2004, 6, 1147.
(7) (a) Hojo, M.; Murakami, C.; Aihara, H.; Komori, E.-i.;
Kohra, S.; Tominaga, Y.; Hosomi, A. Bull. Soc. Chim. Fr.
1995, 132, 499; and references cited therein. (b) Hoke, M.
E.; Brescia, M.-R.; Bogaczyk, S.; DeShong, P.; King, B. W.;
Crimmins, M. T. J. Org. Chem. 2002, 67, 327; and
references cited therein. (c) Denmark, S. E.; Kobayashi, T.
J. Org. Chem. 2003, 68, 5153; and references cited therein.
(d) Seganish, W. M.; DeShong, P. J. Org. Chem. 2004, 69,
6790; and references cited therein. (e) Denmark, S. E.;
Neuville, L. Org. Lett. 2000, 2, 3221. (f) Sahoo, A. K.; Oda,
T.; Nakao, Y.; Hiyama, T. Adv. Synth. Catal. 2004, 346,
1715; and references cited therein. (g) Riggleman, S.;
DeShong, P. J. Org. Chem. 2003, 68, 8106. (h) Seganish,
W. M.; DeShong, P. Org. Lett. 2004, 6, 4379. (i) Wnuk, S.
F.; Garcia, P. I. Jr.; Wang, Z. Org. Lett. 2004, 6, 2047.
(j) Son, E.-C.; Tsuji, H.; Saeki, T.; Tamao, K. Bull. Chem.
Soc. Jpn. 2006, 79, 492.
(8) Reactions using cyclic oligosiloxanes in which one aryl or
vinyl group is attached to a silicon atom have been reported.
See: (a) Denmark, S. E.; Butler, C. R. Org Lett. 2006, 8, 63;
and references cited therein. (b) Mori, A.; Suguro, M.
Synlett 2001, 845.
(9) Takiguchi, T. Bull. Chem. Soc. Jpn. 1959, 32, 556.
(10) In a mortar were placed diphenylsilanediol (3.2 g, 15 mmol)
and PTSA·H2O (7.6 g, 40 mmol), and the mixture was
kneaded well for 1 h. After the mixture was allowed to stand
for 24 h, the resulting crude product was rinsed with CH2Cl2
and H2O (100 mL each) and the rinse was poured into a
separatory funnel. Aqueous layer was extracted with 20 mL
(n) Handy, C. J.; Manoso, A. S.; McElroy, W. T.; Seganish,
W. M.; DeShong, P. Tetrahedron 2005, 61, 12201.
(2) (a) Tamao, K.; Kobayashi, K.; Ito, Y. Tetrahedron Lett.
1989, 30, 6051. (b) Roshchin, A. I.; Bumagin, N. A.;
Beletskaya, I. P. Dokl. Akad. Nauk 1994, 334, 602.
(c) Homsi, F.; Hosoi, K.; Nozaki, K.; Hiyama, T. J.
Organomet. Chem. 2001, 624, 208; and references cited
therein. (d) Ito, H.; Sensui, H.; Arimoto, K.; Miura, K.;
Hosomi, A. Chem. Lett. 1997, 26, 639. (e) Mowery, M. E.;
DeShong, P. J. Org. Chem. 1999, 64, 3266; and references
cited therein. (f) Denmark, S. E.; Pan, W. J. Organomet.
Chem. 2002, 653, 98. (g) Denmark, S. E.; Yang, S.-M.
Tetrahedron 2004, 60, 9695; and references cited therein.
(h) Denmark, S. E.; Tymonko, S. A. J. Am. Chem. Soc. 2005,
127, 8004; and references cited therein. (i) Mori, A.;
Takahisa, E.; Yamamura, Y.; Kato, T.; Mudalige, A. P.;
Kajiro, H.; Hirabayashi, K.; Nishihara, Y.; Hiyama, T.
Organometallics 2004, 23, 1755; and references cited
therein. (j) Itami, K.; Mineno, M.; Kamei, T.; Yoshida, J.
Org. Lett. 2002, 4, 3635; and references cited therein.
(k) Denmark, S. E.; Baird, J. D. Org. Lett. 2006, 8, 793; and
references cited therein. (l) Hosoi, K.; Nozaki, K.; Hiyama,
T. Chem. Lett. 2002, 31, 138. (m) Huang, T.; Li, C.-J.
Tetrahedron Lett. 2002, 43, 403. (n) Penso, M.; Albanese,
D.; Landini, D.; Lupi, V. J. Mol. Catal. A: Chem. 2003, 204–
205, 177. (o) Trost, B. M.; Machacek, M. R.; Ball, Z. Org.
Lett. 2003, 5, 1895. (p) Nokami, T.; Tomida, Y.; Kamei, T.;
Synlett 2007, No. 5, 749–752 © Thieme Stuttgart · New York