Cationic palladium complex-catalyzed cyclization-hydrosilylation of alkadiynes and enynes

Chemistry Letters

Volumn 34, Issue 2, 2005, Pages 160-161

  Wakayanagi, Shigeru ^a   Shimamoto, Takamitsu ^a   Chimori, Motoharu ^a   Yamamoto, Keiji ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CATION; PALLADIUM COMPLEX;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CATALYST; CHEMICAL PROCEDURES; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; HYDROSILYLATION; REACTION ANALYSIS;

EID: 17844367102     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.160     Document Type: Article

References (17)

1. Y. Kawanami and K. Yamamoto, Synlett, 1995, 1232.
2. Y. Kawanami and K. Yamamoto, 43rd Symposium on Organometallic Chemistry, Osaka, Japan, 1996, Abstr., No. PB114.
3. T. Uno, S. Wakayanagi, Y. Sonada, and K. Yamamoto, Synlett, 2003, 1997.
4. For recent and closely related cyclization/hydrosilylation, which is catalyzed by a cationic platinum complex containing bidentate nitrogen ligands, see: X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, and R. A. Widenhoefer, J. Org. Chem., 67, 2778 (2002), and references cited therein; Also, for the preceding rhodium-catalyzed silylative cyclization of 1,6-heptadiyne dertivatives with trialkylsilanes, see T. Maruoka, I. Matsuda, and K. Itoh, Organometallics, 21, 3650 (2002); T. Maruoka, I. Matsuda, and K. Itoh, Tetrahedron Lett., 39, 7325 (1998); I. Ojima, A. T. Vu, J. V. McCullagh, and A. Kinoshita, J. Am. Chem. Soc., 121, 3230 (1999); C. Liu and R. A. Widenhoefer, Organometallics, 21, 5666 (2002).
5. For recent and closely related cyclization/hydrosilylation, which is catalyzed by a cationic platinum complex containing bidentate nitrogen ligands, see: X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, and R. A. Widenhoefer, J. Org. Chem., 67, 2778 (2002), and references cited therein; Also, for the preceding rhodium-catalyzed silylative cyclization of 1,6-heptadiyne dertivatives with trialkylsilanes, see T. Maruoka, I. Matsuda, and K. Itoh, Organometallics, 21, 3650 (2002); T. Maruoka, I. Matsuda, and K. Itoh, Tetrahedron Lett., 39, 7325 (1998); I. Ojima, A. T. Vu, J. V. McCullagh, and A. Kinoshita, J. Am. Chem. Soc., 121, 3230 (1999); C. Liu and R. A. Widenhoefer, Organometallics, 21, 5666 (2002).
6. For recent and closely related cyclization/hydrosilylation, which is catalyzed by a cationic platinum complex containing bidentate nitrogen ligands, see: X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, and R. A. Widenhoefer, J. Org. Chem., 67, 2778 (2002), and references cited therein; Also, for the preceding rhodium-catalyzed silylative cyclization of 1,6-heptadiyne dertivatives with trialkylsilanes, see T. Maruoka, I. Matsuda, and K. Itoh, Organometallics, 21, 3650 (2002); T. Maruoka, I. Matsuda, and K. Itoh, Tetrahedron Lett., 39, 7325 (1998); I. Ojima, A. T. Vu, J. V. McCullagh, and A. Kinoshita, J. Am. Chem. Soc., 121, 3230 (1999); C. Liu and R. A. Widenhoefer, Organometallics, 21, 5666 (2002).
7. For recent and closely related cyclization/hydrosilylation, which is catalyzed by a cationic platinum complex containing bidentate nitrogen ligands, see: X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, and R. A. Widenhoefer, J. Org. Chem., 67, 2778 (2002), and references cited therein; Also, for the preceding rhodium-catalyzed silylative cyclization of 1,6-heptadiyne dertivatives with trialkylsilanes, see T. Maruoka, I. Matsuda, and K. Itoh, Organometallics, 21, 3650 (2002); T. Maruoka, I. Matsuda, and K. Itoh, Tetrahedron Lett., 39, 7325 (1998); I. Ojima, A. T. Vu, J. V. McCullagh, and A. Kinoshita, J. Am. Chem. Soc., 121, 3230 (1999); C. Liu and R. A. Widenhoefer, Organometallics, 21, 5666 (2002).
8. For recent and closely related cyclization/hydrosilylation, which is catalyzed by a cationic platinum complex containing bidentate nitrogen ligands, see: X. Wang, H. Chakrapani, J. W. Madine, M. A. Keyerleber, and R. A. Widenhoefer, J. Org. Chem., 67, 2778 (2002), and references cited therein; Also, for the preceding rhodium-catalyzed silylative cyclization of 1,6-heptadiyne dertivatives with trialkylsilanes, see T. Maruoka, I. Matsuda, and K. Itoh, Organometallics, 21, 3650 (2002); T. Maruoka, I. Matsuda, and K. Itoh, Tetrahedron Lett., 39, 7325 (1998); I. Ojima, A. T. Vu, J. V. McCullagh, and A. Kinoshita, J. Am. Chem. Soc., 121, 3230 (1999); C. Liu and R. A. Widenhoefer, Organometallics, 21, 5666 (2002).
9. (S)-2′-Methoxy-2-diphenylphosphino-1,1′-binaphthyl: We thank Professor Hayashi (Kyoto Univ.) for his help.
10. 3) δ 13.9 (q), 14.3 (t), 18.2 (q), 37.6 (d), 40.0 (t), 41.7 (d), 58.0 (s), 58.3 (t), 61.3 (t), 106.1 (t), 154.1 (s), 171.9 (s), 171.8 (s).
11. 13CNMR δ 8.1, 14.6, 17.9, 18.3, 42.8, 58.5, 69.8, 70.7, 115.2, 142.2. The major component may have (R*,R*) on the basis of cis-carbopalladation to take place.
12. 13CNMR δ 18.1, 28.7, 34.1, 34.2, 58.4, 72.8, 74.3, 108.4, 114.7, 126.4, 138.6, 143.2, 150.5.
13. 13CNMR δ 14.8. 18.3, 23.9, 28.7, 34.8, 39.7, 56.8, 58.3, 67.5, 74.1, 80.1, 114.8, 154.8. Characterized by an OFR measurement.
14. The substrate containing a terminal alkyne site tends to give an expected cyclization product in a poor yield, due to high bp byproduct.
15. To the best of our knowledge, reversibility of the hydropalladation in Pd-catalyzed cyclization-hydrosilylation of alkadiynes has not been established. However, reversible silylpalladation in the case of alkadienes under similar reaction conditions are discussed: X. Wang, H. Chakrapani, C. N. Stengone, and R. A. Widenhoefer, J. Org. Chem., 66, 1755 (2001).
16. Y. Maruyama, K. Yamamura, T. Sagawa, H. Katayama, and F. Ozawa, Organometallics, 19, 1308 (2002); For a pertinent review, see F. Ozawa, J. Organomet. Chem., 611, 332 (2000).
17. Y. Maruyama, K. Yamamura, T. Sagawa, H. Katayama, and F. Ozawa, Organometallics, 19, 1308 (2002); For a pertinent review, see F. Ozawa, J. Organomet. Chem., 611, 332 (2000).